Benzyl Bromide → HCID 22482458, compound

HRID 841539Notes

Reaction equation

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

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 178488935HCID 178488935, compound

Product 1

HCID 22482458HCID 22482458, compoundYield 90.7%

Procedure

2-(2,6-Difluorophenyl)-4-methoxylbenzimidazole (5005, Example 46) (2.02 g, 7.77 mmol) was reacted with benzyl bromide (1.20 mL, 10.1 mmol, 130 M%). The crude product was purified by flash chromatography eluting with 2% MeOH/CH2Cl2 and recrystallization from diethylether/hexane (3:1), yielding white crystals of 1-benzyl-2-(2.6-difluorophenyl)-4-methoxylbenzimidazole (2.47 g, 7.05 mmol, 90% yield). M.p. 139-141° C. 1H-NMR (200 MHz, CD2Cl2) δ7.48 (m, 1H, H4′), 7.25-6.96 (m, 8H), 6.86 (dd, J=0.8, 8.3 Hz, 1H, H5), 6.72 (dd, J=8.0, 0.8 Hz, 1H, H7), 5.24 (s, 2H, CH2Ph), 4.01 (s, 3H, OCH3).

Workup

customThe crude product was purified by flash chromatography
washeluting with 2% MeOH/CH2Cl2 and recrystallization from diethylether/hexane (3:1)

Sources & evidence

ORD record: ord-d2a4b508d45b4103a1afd940090cd151
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369235B1

Reaction notes

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