2-Bromoethanol → HCID 68567423, compound

HRID 1435108Notes

Reaction equation

[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:23]=3[Cl:29])[CH3:21])[CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:30][CH2:31][CH2:32]O>>[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:32][CH2:31][Br:30])[C:23]=3[Cl:29])[CH3:21])[CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Reactant 2

HCID 108982-Bromoethanol

HCID 68569908HCID 68569908, compound2×

Product 1

HCID 68567423HCID 68567423, compoundYield 71%

Procedure

Methyl 5-(1H-benzimidazol-1-yl)-3-{[(1R)-1-(2-chloro-3-hydroxyphenyl)ethyl]oxy}-2-thiophenecarboxylate (Intermediate 11A, 600 mg, 1.4 mmol) and 2-bromoethanol (120 μL, 1.7 mmol) were coupled using a procedure analogous to Example 4, Step A to give 529 mg of the title compound (71%), 1H NMR (400 MHz, d6-DMSO) δ 8.85 (s, 1H), 7.77 (d, J=7.2 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.39-7.31 (m, 5H), 7.10 (dd, J=8.0 and 1.6 Hz, 1H), 5.98 (m, 1H), 4.40-4.37 (m, 2H), 3.81-3.79 (m, 5H), 1.81 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record: ord-a5fea0f9c84245ab95ce69bf6ae84299
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615643B2

Reaction notes

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