Dichloromethane → HCID 71008962, compound

HRID 1887482Notes

Reaction equation

HRID 1887482 reaction equation
Cl.[F:2][C:3]([F:22])([F:21])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]3[CH2:17][NH:18][CH2:19][CH:13]3[C:12]2=[O:20])=[CH:7][CH:6]=1.Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.CCN(CC)CC.ClCCl>CO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:18]2[CH2:17][CH:14]3[CH:13]([C:12](=[O:20])[N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][C:3]([F:2])([F:21])[F:22])=[CH:6][CH:7]=4)[CH2:16][CH2:15]3)[CH2:19]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 680214-Fluorobenzyl bromideHCID 131730790HCID 131730790, compound

Product 1

HCID 71008962HCID 71008962, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Trifluoromethoxy-phenyl)-octahydro-pyrrolo[3,4-c]pyridin-4-one, hydrochloride (80 mg, 0.24 mmol), 1-(bromomethyl)-4-fluorobenzene (90 mg, 0.48 mmol) and Et3N (0.12 g, 1.2 mmol) were added to dichloromethane (2 mL), and the mixture was stirred for 12 h. The product (30 mg, 31%) was obtained by prep-TLC (eluting with dichloromethane: MeOH=25:1). 1H NMR (300 MHz, CDCl3): δ 7.48-7.44 (m, 2H), 7.29-7.09 (m, 6H), 4.23-4.19 (m, 2H), 3.85-3.25 (m, 7H), 2.50-2.48 (m, 1H), 2.28-2.24 (m, 1H), 1.25-1.23 (m, 1H); LC-MS: [M+1]+ 409.1.

Sources & evidence

ORD record
ord-a241b3a9f3034e2f8c1c67ba61d25781
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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