Ethanol → Ethyl 3-[4-(1H-benzimidazol-2-ylcarbonyl)phenoxy]-2-pyrazinecarboxylate

HRID 887489Notes

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](Cl)=[N: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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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]([C:26]([O:29][CH2:31][CH3:32])=[O:28])=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

Conditions

Temperature: 135 °C

Procedure

In a 2 L autoclave was added a solution (1H-benzo[d]imidazol-2-yl)(4-(3-chloropyrazin-2-yloxy)phenyl)methanone (5.0 g, 14.2 mmol) in ethanol (150 mL), followed by dppf (0.273 g, 0.42 mmol), palladium acetate (25 mg, 0.11 mmol) and sodium acetate (4.65 g, 56.8 mmol). The autoclave was applied CO(g) 15 kg/cm2 pressure. Then the reaction mixture was heated to 135° C. and maintained at that temperature for 1 h. After cooling to RT, the reaction mixture was concentrated and diluted with water, then extracted by ethyl acetate (3×200 mL). The combined organic extracts were dried over sodium sulfate and concentrate under vacuum to give a dark brown solid which was used directly in the following step. MS [M+H]=389.1.

Workup

temperaturemaintained at that temperature for 1 h
temperatureAfter cooling to RT
concentrationthe reaction mixture was concentrated
additiondiluted with water
extractionextracted by ethyl acetate (3×200 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrate under vacuum
customto give a dark brown solid which

Sources & evidence

ORD record: ord-8d9bcd0aefa247b0a0b4c5ba3706ab4b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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