Ethanol → HCID 59327218, compound

HRID 410329Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[C:26]([O-:29])(=[O:28])C.[Na+].[CH2:31](O)[CH3:32]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[N:20]=[CH:21][CH:22]=[CH:23][C:24]=2[C:26]([O:29][CH2:31][CH3:32])=[O:28])=[CH:14][CH:13]=1)=[O:11]

Participants

Conditions

Temperature: 135 °C

Procedure

To the solution of (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone. (17.0 g, 43.1 mmol) in ethanol (600 mL) was added dppf (0.716 g, 1.29 mmol) and Pd(OAc)2 (77 mg, 0.344 mmol) and sodium acetate (14.13 g, 172 mmol) in 2.0 L. autoclave and apply CO(g) 15 kg/cm2 pressure. Then the reaction mixture was heated up to 135° C. and maintained at that temperature for 1 h. The reaction mass was concentrated under vacuum and diluted with water, then extracted by ethyl acetate (3×500 mL). The combined organic extracts were dried over sodium sulfate and concentrate under vacuum to give the title compound as dark brown solid. MS (ESI, pos. ion) m/z: 389.1 (M+1).

Workup

temperaturemaintained at that temperature for 1 h
concentrationThe reaction mass was concentrated under vacuum
additiondiluted with water
extractionextracted by ethyl acetate (3×500 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrate under vacuum

Sources & evidence

ORD record: ord-5907cd904a23435cb41894a061d2a0ca
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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