Cesium carbonate → HCID 117641968, compound

HRID 922769Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH:17]=[C:16]([C@@:18]([OH:25])([CH2:23][CH3:24])[C:19]([F:22])([F:21])[F:20])[N:15]=[N:14]3)=[CH:9][CH:10]=2)[N:5]=[C:4]([C:26]([NH2:28])=[O:27])[CH:3]=1.[F:29][C:30]1[CH:31]=[CH:32][C:33](B(O)O)=[N:34][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].[Cu]Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:29][C:30]1[CH:31]=[CH:32][C:33]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH2:12][N:13]4[CH:17]=[C:16]([C@@:18]([OH:25])([CH2:23][CH3:24])[C:19]([F:20])([F:22])[F:21])[N:15]=[N:14]4)=[CH:9][CH:10]=3)[N:5]=[C:4]([C:26]([NH2:28])=[O:27])[CH:3]=2)=[N:34][CH:35]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-chloro-7-({4-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carboxamide (3-14, 16.0 mg, 0.039 mmol, 1.0 equiv), (5-fluoropyridin-2-yl)boronic acid (22 mg, 0.097 mmol, 2.5 equiv), cesium carbonate (25 mg, 0.077 mmol, 2.0 equiv), DPPF (2.1 mg, 0.004 mmol, 0.1 equiv), copper(I) chloride (3.8 mg, 0.039 mmol, 1.0 equiv) and palladium(II) acetate (0.43 mg, 0.002 mmol, 0.05 equiv) were combined and purged with argon. DMF (0.4 mL) was added and the mixture was heated at 100° C. for 14 hours. The mixture was filtered purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier) to afford 4-(5-fluoropyridin-2-yl)-7-({4-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carboxamide (3-16) as a white solid. LRMS m/z (M+H)+ 475.1 found, 475.2 required

Workup

custompurged with argon
additionDMF (0.4 mL) was added
filtrationThe mixture was filtered
custompurified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier)

Sources & evidence

ORD record: ord-6ce276e74cdb4edb917e570ec364fb1a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

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