Toluene → HCID 86690475, compound

HRID 1026750Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][CH:10]([CH3:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[F:12][C:11]([F:14])([F:13])[CH:10]([NH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[CH:7]=1)[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-[(2-bromopyridin-4-yl)methyl]-1,1,1-trifluoropropan-2-amine (150 mg), 4-fluorophenylboronic acid (111 mg), cesium carbonate (345 mg), tetrakis(triphenylphosphine)palladium (61 mg), toluene (0.6 mL), ethanol (0.6 mL) and water (4.0 mL) was stirred while heating at 100° C. for 3 hr. The supernatant of the reaction mixture was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=95:5-60:40) to afford the title compound (143 mg).

Workup

customThe supernatant of the reaction mixture was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=95:5-60:40)

Sources & evidence

ORD record: ord-80b8a32cf8c546dd9cebf03afd78a3d3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729271B2

Reaction notes

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