Water → HCID 86731324, compound

HRID 2277253Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[CH:19][CH:18]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1COCC1.[Cu](I)I>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[O:28][C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)=[CH:19][CH:18]=3)=[N:15][C:12]2=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-(5-(benzyloxy)-3-bromopyridin-2-yl)-4-(cyclopropylmethoxy)benzamide (780 mg) in THF (10 mL) were added copper iodide (49.2 mg), 1,10-phenanthroline (93.0 mg) and cesium carbonate (1.12 g), and the mixture was stirred with heating overnight at 70° C. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (157 mg).

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-6015ad29f62d4c6298cac51d11603997
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

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