Cyclohexanone → Methyl 3-cyclohexyl-1H-indole-6-carboxylate

HRID 747931Notes

Reaction equation

HRID 747931 reaction equation
N1C2C(=CC=C(C(O)=O)C=2)C=[CH:2]1.C1(=O)CCCCC1.[C:20]1([C:26]2[C:34]3[C:29](=[CH:30][C:31]([C:35]([OH:37])=[O:36])=[CH:32][CH:33]=3)[NH:28][CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1>>[CH:20]1([C:26]2[C:34]3[C:29](=[CH:30][C:31]([C:35]([O:37][CH3:2])=[O:36])=[CH:32][CH:33]=3)[NH:28][CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 5952301H-indole-6-carboxylic acidHCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

Product 1

HCID 11230631Methyl 3-cyclohexyl-1H-indole-6-carboxylate

Procedure

Condensation of 1H-indole-6-carboxylic acid with cyclohexanone can generate 3-cyclohexenyl-1H-indole-6-carboxylic acid. This indole ester can be subjected to sequential reduction and esterification to provide methyl 3-cyclohexanyl-1H-indole-6-carboxylate.

Sources & evidence

ORD record
ord-322959282f144f4abb57f76d4ed14633
Source dataset
uspto-grants-2008_07
Patent number
US07399758B2

Reaction notes

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