Sodium Iodide → HCID 69068939, compound

HRID 2111784Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[Na+].[I-].[F:29][C:30]([F:41])([F:40])[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1>CN(C=O)C>[F:29][C:30]([F:40])([F:41])[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=4[N:10]=[CH:9]3)=[CH:6][CH:7]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 0.2M DMF solution of methyl 1-(4-hydroxyphenyl)-1H-benzimidazole-5-carboxylate (3.0 g, 9.8 mmol) with KOtBu (2.2 g, 19.6 mmol) was stirred at rt for 20 min. prior to treatment with NaI (9.8 mmol, 1.47 g) and p-(trifluoromethoxy) benzylbromide (1.88 mL, 11.2 mmol). The mixture was heated at 60° C. for 24 h. after which the mixture was concentrated in vacuo, and the residue purified by chromatography over silica gel eluting with 1:1 EtOAc:Hexane to afford methyl 1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxylate. 1H NMR (DMSO-d6, 400 MHz) δ 3.89 (s, 3H), 5.26 (s, 2H), 7.26-7.29 (m, 2H), 7.43 (d, 2H, J=7.6 Hz), 7.61-7.65 (m, 5H), 7.86 (dd, 1H, J=8.8 Hz, 1.6 Hz), 8.35 (d, 1H, J=1.2 Hz), 8.65 (s, 1H); MS (ES+): m/z 443 (MH+).

Workup

concentrationwas concentrated in vacuo
customthe residue purified by chromatography over silica gel eluting with 1:1 EtOAc

Sources & evidence

ORD record: ord-6b54bb0dfa6d420884b8b9dcd1c2e8dd
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521448B2

Reaction notes

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