Cyclopentylacetic acid → Methyl 4-[5-bromo-6-cyclopentylacetamidoindol-1-ylmethyl]-3-methoxybenzoate

HRID 358744Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][C:3]=1[Br:24].[CH:25]1([CH2:30][C:31](O)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26]1>>[Br:24][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][C:31](=[O:32])[CH2:30][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[N:8]([CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23])[CH:7]=[CH:6]2

Participants

Reactant 2

HCID 71606Cyclopentylacetic acid

HCID 19744364HCID 19744364, compound

Product 1

HCID 19744399Methyl 4-[5-bromo-6-cyclopentylacetamidoindol-1-ylmethyl]-3-methoxybenzoateYield 60%

Procedure

Using a similar procedure to that described in Example 185, but starting from methyl 4-(6-amino-5-bromoindol-1-ylmethyl)-3-methoxybenzoate (GG) and cyclopentylacetic acid, methyl 4-[5-bromo-6-cyclopentylacetamidoindol-1-ylmethyl]-3-methoxybenzoate was obtained in 60% yield as an off-white solid; partial NMR: 1.6 [br m,8H,(CH2)4 ], 3.8 (s,3H,OCH3), 3.9 (s,3H,OCH3), 5.3 (s,2H,NCH2), 6.4 (dd,1H,H3-indole), 7.1 (d,1H,H2 -indole), 7.7 (br, 1H,NH), 7.8 (s,1H,H4 -indole), 8.5 (br s,1H,H7 -indole).

Sources & evidence

ORD record: ord-d485f67117304371999d4aa03b3f6730
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997844

Reaction notes

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