trans-2-[4-(Trifluoromethyl)phenyl]vinylboronic acid → HCID 68751801, compound

HRID 1912957Notes

Reaction equation

HRID 1912957 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/B(O)O)=[CH:5][CH:4]=1.Br[C:17]1[C:18]([NH:26][C:27](=[O:35])[CH2:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[N:19][N:20]2[CH:25]=[CH:24][CH:23]=[N:22][C:21]=12>>[CH:30]1([CH2:29][CH2:28][C:27]([NH:26][C:18]2[C:17](/[CH:10]=[CH:9]/[C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=3)=[C:21]3[N:22]=[CH:23][CH:24]=[CH:25][N:20]3[N:19]=2)=[O:35])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 6153620trans-2-[4-(Trifluoromethyl)phenyl]vinylboronic acidHCID 68752925N-(3-bromopyrazolo[1,5-a]pyrimidin-2-yl)-3-cyclopentylpropanamide

Product 1

HCID 68751801HCID 68751801, compound

Procedure

Trans-2-[4-(trifluoromethyl)phenyl]vinylboronic acid and the product from Example 153A 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 10.32-10.34 (bs, 1H), 9.10 (dd, J=6.9, 1.7 Hz, 1H), 8.69 (dd, J=4.1, 1.7 Hz, 1H), 7.70 (s, 4H), 7.64 (d, J=16.3 Hz, 1H), 7.34 (d, J=16.2 Hz, 1H), 7.14 (dd, J=6.9, 4.1 Hz, 1H), 2.49 (t, J=7.9 Hz, 2H), 1.76-1.86 (m, 3H), 1.45-1.70 (m, 6H), 1.07-1.18 (m, 2H); MS (ESI) m/z 429 (M+H)+.

Sources & evidence

ORD record
ord-b5d400ebd35e4083abc06fbf098ac6f0
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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