6-fluoro-3-(piperidin-4-yl)-1H-indole → 5-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-2-methoxy-benzoic acid ethyl ester

HRID 457815Notes

Reaction equation

HRID 457815 reaction equation
F[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([CH2:27]Br)[CH:24]=[CH:23][C:22]=1[O:29][CH3:30])[CH3:18]>>[CH2:17]([O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([CH2:27][N:14]2[CH2:15][CH2:16][CH:11]([C:6]3[C:5]4[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=4)[NH:8][CH:7]=3)[CH2:12][CH2:13]2)[CH:24]=[CH:23][C:22]=1[O:29][CH3:30])[CH3:18]

Participants

3

Reactant 2

HCID 110960776-fluoro-3-(piperidin-4-yl)-1H-indoleHCID 688939465-Bromomethyl-2-methoxybenzoic acid ethyl ester

Product 1

HCID 694122085-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-2-methoxy-benzoic acid ethyl esterYield 91%

Procedure

This compound was prepared following the procedure described in example 1 (part D) starting with 0.5 g (2.5 mmol) of 6-fluoro-3-piperidin-4-yl-1H-indole and 0.88 g (3.2 mmol) of 5-bromomethyl-2-methoxy-benzoic acid ethyl ester. After standard purification, 0.83 g (91% of yield) of 5-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-2-methoxy-benzoic acid ethyl ester were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter standard purification

Sources & evidence

ORD record
ord-a83d0b862daa4cb488e2ed90f94dabba
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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