Bis(neopentyl glycolato)diboron → HCID 10177515, compound
Reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)COB([C:22]2[CH:23]=[CH:24][C:25]([F:35])=[C:26]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][C:33]=3[F:34])[CH:27]=2)OC1.FC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1C1C(C#N)=CC=CC=1.B1(B2OCC(C)(C)CO2)OCC(C)(C)CO1>[Pd]>[F:35][C:25]1[CH:24]=[CH:23][C:22]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:27][C:26]=1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1[F:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled to 3-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-4-fluoropyridine (prepared in an analogous manner to 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile in Example 1, using bis(neopentyl glycolato)diboron instead of bis(pinacolato)diboron in the final palladium coupling) using the procedure described in Example 65. 3-[4-Fluoro-3-(4-fluoropyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine was isolated as a yellow solid in 36% yield after purification on silica gel eluting with dichloromethane on a gradient of diethyl ether (2-15%): δH (400 MHz, DMSO) 7.48-7.55 (2H, m), 7.63 (1H, dd, J 10 and 9), 7.94 (1H, ddd, J 9, 5 and 2), 7.99 (1H, dd, J 7 and 2), 8.33 (1H, s), 8.73 (1H, dd, J 8 and 5.5), 8.85 (1H, d, J 10), 9.38 (1H, d, J 7); m/z (ES+) 377 (M++H).
Sources & evidence
- ORD record
- ord-fe27f1d70de94daebc2daea1a9f464f0
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900215B2
Reaction notes
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