3,3-Dimethyl-1-butenylboronic acid → N-{3-[(1E)-3,3-dimethylbut-1-en-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl}-2-(4-fluorophenyl)acetamide

HRID 1912961Notes

Reaction equation

HRID 1912961 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.[CH3:22][C:23]([CH3:30])([CH3:29])[CH:24]=[CH:25]B(O)O>>[CH3:22][C:23]([CH3:30])([CH3:29])/[CH:24]=[CH:25]/[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

Participants

3

Reactant 2

HCID 27632983,3-Dimethyl-1-butenylboronic acidHCID 68749921N-(3-bromopyrazolo[1,5-a]pyrimidin-2-yl)-2-(4-fluorophenyl)acetamide

Product 1

HCID 68748259N-{3-[(1E)-3,3-dimethylbut-1-en-1-yl]pyrazolo[1,5-a]pyrimidin-2-yl}-2-(4-fluorophenyl)acetamide

Procedure

The product from Example 140A and 3,3-dimethyl-1-butenylboronic acid were processed using the method analogous to that described in Example 110C to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.32-10.43 (bs, 1H), 8.99 (dd, J=7.0, 1.7 Hz, 1H), 8.56 (dd, J=4.1, 1.7 Hz, 1H), 7.37-7.43 (m, 2H), 7.13-7.21 (m, 2H), 7.04 (dd, J=7.0, 4.1 Hz, 1H), 6.63 (d, J=16.3 Hz, 1H), 6.08 (d, J=16.5 Hz, 1H), 3.70 (s, 2H), 1.01 (s, 9H); MS (APCI) m/z 353 (M+H)+.

Sources & evidence

ORD record
ord-8186599a7d2c4578b2d081489185b93a
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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