4-Fluorobenzylamine → 2-chloro-6-(4-fluorobenzyl)-5H-pyrrolo[3,4-b]pyridin-7(6H)-one

HRID 2201580Notes

Reaction equation

HRID 2201580 reaction equation
Br[CH2:2][C:3]1[C:4]([C:10]([O:12]C)=O)=[N:5][C:6]([Cl:9])=[CH:7][CH:8]=1.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>CO>[Cl:9][C:6]1[N:5]=[C:4]2[C:10](=[O:12])[N:20]([CH2:19][C:18]3[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=3)[CH2:2][C:3]2=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 582166312-Pyridinecarboxylic acid, 3-(bromomethyl)-6-chloro-, methyl ester

Product 1

HCID 1177716762-chloro-6-(4-fluorobenzyl)-5H-pyrrolo[3,4-b]pyridin-7(6H)-oneYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-(bromomethyl)-6-chloropicolinate (100 mg, 0.38 mmol) and 4-fluorobenzylamine (237 mg, 1.89 mmol) in MeOH (10 mL) was stirred at 15° C. overnight. After the reaction, it was filtered to afford crude 2-chloro-6-(4-fluorobenzyl)-5H-pyrrolo[3,4-b]pyridin-7(6H)-one (75 mg, yield: 72%). 1H-NMR (CDCl3, 400 MHz) δ 7.73 (d, J=8.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.28˜7.31 (m, 2H), 7.05 (t, J=8.4 Hz, 2H), 4.82 (s, 2H), 4.25 (s, 2H). MS (M+H)+: 277/279.

Workup

  1. customAfter the reaction, it
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-c17ef7279056428bbe42c6da9604b074
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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