Cesium carbonate → HCID 86683086, compound

HRID 1497271Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:3]=1[C:21]#[N:22].[CH3:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.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>[CH:16]1([C:4]2[C:3]([C:21]#[N:22])=[C:2]([C:28]3[CH:27]=[CH:26][N:25]=[C:24]([CH3:23])[CH:29]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=3)[N:5]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 4-bromo-2-cyclopentyl-6-trifluoromethyl-quinoline-3-carbonitrile (130 mg, 352 μmol), 2-methylpyridine-4-boronic acid pinacol ester (92.6 mg, 423 μmol), cesium carbonate (103 mg, 317 μmol) and tetrakis(triphenylphosphine)palladium (0) (40.7 mg, 35.2 μmol) in DMF (5.2 ml) was heated to 90° C. for 16 h. The reaction mixture was poured on water and extracted with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, n-heptane/EtOAc 4:1) to afford the title compound (20 mg, 15%) as off-white solid. MS (ESI): 382.6 (M+H)+.

Workup

additionThe reaction mixture was poured on water
extractionextracted with EtOAc
washThe combined extracts were washed with water and brine
dry with materialdried with Na2SO4
customevaporated
customThe remaining solid was purified by column chromatography (silica gel, n-heptane/EtOAc 4:1)

Sources & evidence

ORD record: ord-1bac39c5a45a40a4892e15f3932e7f55
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

Loading…