4-(Trifluoromethoxy)phenylboronic acid → 2-(4-fluorophenyl)-N-{3-[4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-2-yl}acetamide

HRID 1912944Notes

Reaction equation

HRID 1912944 reaction equation
Br[C:2]1[C:3]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[N:7][C:6]=12.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12]([NH:11][C:3]2[C:2]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]([F:22])([F:34])[F:35])=[CH:30][CH:29]=3)=[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][N:5]3[N:4]=2)=[O:21])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 68749921N-(3-bromopyrazolo[1,5-a]pyrimidin-2-yl)-2-(4-fluorophenyl)acetamide

Product 1

HCID 687557012-(4-fluorophenyl)-N-{3-[4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-2-yl}acetamide

Procedure

The product from Example 140A and 4-trifluoromethoxyphenylboronic acid were processed using the method analogous to that described in example 110C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.29-10.76 (bs, 1H), 9.11 (dd, J=6.9, 1.7 Hz, 1H), 8.63 (dd, J=4.1, 1.7 Hz, 1H), 7.75-7.78 (m, 2H), 7.32-7.39 (m, 2H), 7.24-7.29 (m, 2H), 7.14-7.19 (m, 3H), 3.67 (s, 2H); MS (APCI) m/z 431 (M+H)+. Anal. calculated for C21H14F4N4O2: C, 58.61; H, 3.28; N, 13.02. Found C, 58.37; H, 2.91; N, 12.81.

Sources & evidence

ORD record
ord-2f908325da334433b933ba6814215bdf
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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