6-Amino-3-bromopyridine-2-carbonitrile → 6-Amino-3-(2'-(cyclopropylsulfonyl)-3-fluoro-[1,1'-biphenyl]-4-yl)picolinonitrile
Reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[C:15]([F:28])[CH:14]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:29][C:30]1[N:35]=[C:34]([C:36]#[N:37])[C:33](Br)=[CH:32][CH:31]=1>>[NH2:29][C:30]1[N:35]=[C:34]([C:36]#[N:37])[C:33]([C:16]2[CH:17]=[CH:18][C:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[CH:14][C:15]=2[F:28])=[CH:32][CH:31]=1Participants
3
Procedure
The title compound was prepared using analogous conditions to those described in Example 6 2-(2′-(cyclopropylsulfonyl)-3-fluoro-[1,1′-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 6-amino-3-bromo-2-cyanopyridine. MS (ESI): mass calcd. for C21H16FN3O2S, 393.09; m/z found, 393.9 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.07 (d, J=7.9, 1H), 7.71-7.64 (m, 1H), 7.64-7.58 (m, 2H), 7.54-7.48 (m, 1H), 7.40 (dd, J=19.2, 9.2, 2H), 7.33 (dd, J=7.9, 1.6, 1H), 6.86 (d, J=8.7, 1H), 6.79 (d, J=10.0, 3H), 1.03 (s, 9H).
Sources & evidence
- ORD record
- ord-13323526857d4be7b15175a493d91b2d
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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