Claims
- 1. The process for producing the compounds having the structure ##STR6## wherein R.sup.1 is hydrogen, lower alkyl containing 1 to 4 carbon atoms or halogen; R.sup.2 is lower alkyl containing 1 to 4 carbon atoms and the pharmaceutically acceptable salts thereof which comprises
- (a) successively triflating, heating with lithium iodide, and reducing the compound of structure ##STR7## wherein R.sup.1 is as defined above to produce the amine of structure ##STR8## wherein R.sup.1 is as defined above (b) reacting said amine with HNO.sub.2 and SnCl.sub.2 to produce the hydrazine of structure ##STR9## wherein R.sup.1 is as defined above (c) reacting said hydrazine with dihydrofuran to produce the corresponding hydrazone and in the presence of zinc chloride converting the hydrazone to the corresponding tryptophol of structure ##STR10## wherein R.sup.1 is as defined above (d) cyclizing said tryptophol with methyl 3-methoxy-2-pentenoate in the presence of boron trifluoride etherate or with methyl propionyl acetate in the presence of p-toluenesulfuric acid to produce the indole of structure ##STR11## wherein R.sup.1 is as defined above (e) reacting said indole with copper (I) alkyl acetylide to produce the ester of structure ##STR12## wherein R.sup.1 and R.sup.2 are as defined above (f) hydrogenating said propynyl derivative to produce the compound of structure ##STR13## wherein R.sup.1 and R.sup.2 are as defined above (g) hydrolyzing said ester to produce the desired compound of structure (1) and optionally converting said compound to a phrmaceutically acceptable salt.
- 2. The process according to claim 1 in which in step (e) the compound of structure ##STR14## is alkylated with copper (I) methyl acetylide to produce the compound of structure ##STR15##
- 3. The process according to claim 1 in which in step (e) the compound of structure ##STR16## is alkylated with copper (I) methyl acetylide to produce the compound of structure ##STR17##
- 4. A process according to claim 1 in which in step (f) the compound of structure ##STR18## is hydrogenated using Lindlar catalyst to produce the compound of structure ##STR19##
- 5. A process according to claim 1 in which in step (f) the compound of structure ##STR20## is hydrogenated using Lindlar catalyst to produce the compound of structure ##STR21##
Priority Claims (1)
Number |
Date |
Country |
Kind |
548883 |
Oct 1987 |
CAX |
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Parent Case Info
This is a division of application Ser. No. 201,010, filed June 1, 1988, now U.S. Pat. No. 4,822,781.
US Referenced Citations (5)
Number |
Name |
Date |
Kind |
3843681 |
Demerson et al. |
Oct 1974 |
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3939178 |
Demerson et al. |
Feb 1976 |
|
3974179 |
Demerson et al. |
Aug 1976 |
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4585877 |
Demerson et al. |
Apr 1986 |
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4785015 |
McKittrick et al. |
Nov 1988 |
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Non-Patent Literature Citations (1)
Entry |
R. Morrison et al., Organic Chemistry, Second edition, p. 156, Allyn and Bacon, Boston (1967). |
Divisions (1)
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Number |
Date |
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Parent |
201010 |
Jun 1988 |
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