Methyl 2-(bromomethyl)-4-methoxybenzoate → 4-methoxy-2-[4-(5-methoxy-1-thiophen-2-ylmethyl-1H-indol-3-yl)-piperidin-1-ylmethyl]-benzoic acid

HRID 457853Notes

Reaction equation

HRID 457853 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH:7]=[C:6]2[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C[O:25][C:26](=[O:37])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[CH2:35]Br>>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([OH:37])=[O:25])=[C:28]([CH2:35][N:21]2[CH2:22][CH2:23][CH:18]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH2:12][C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[CH:7]=3)[CH2:19][CH2:20]2)[CH:29]=1

Participants

3

Reactant 2

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoateHCID 179643805-methoxy-3-piperidin-4-yl-1-thiophen-2-ylmethyl-1H-indole

Product 1

HCID 179643544-methoxy-2-[4-(5-methoxy-1-thiophen-2-ylmethyl-1H-indol-3-yl)-piperidin-1-ylmethyl]-benzoic acid

Procedure

This compound was prepared following the procedure described in example 13 (part D) starting with 0.06 g (0.19 mmol) of 5-methoxy-3-piperidin-4-yl-1-thiophen-2-ylmethyl-1H-indole (example 89, part B) and 0.064 g (0.23 mmol) of 2-bromomethyl-4-methoxy-benzoic acid methyl ester. After standard work-up and purification by chromatography using a C18 column, 0.018 g (19% of yield) of the expected acid were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter standard work-up and purification by chromatography

Sources & evidence

ORD record
ord-29dec2c03e5344f38b669db59ed273f5
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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