trans-2-(4-Chlorophenyl)vinylboronic acid → N-{3-[(E)-2-(4-chlorophenyl)vinyl]pyrazolo[1,5-a]pyrimidin-2-yl}-3,3-dimethylbutanamide

HRID 1912913Notes

Reaction equation

HRID 1912913 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][C:4]([NH:6][C:7]1[C:15]([C:16]2C=N[CH:19]=[CH:20][CH:21]=2)=[C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:9]2[N:8]=1)=[O:5].[Cl:24][C:25]1[CH:30]=CC(/C=C/B(O)O)=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:30]=[CH:19][C:20](/[CH:21]=[CH:16]/[C:15]2[C:7]([NH:6][C:4](=[O:5])[CH2:3][C:2]([CH3:1])([CH3:22])[CH3:23])=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[N:11][C:10]=23)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 642694trans-2-(4-Chlorophenyl)vinylboronic acidHCID 687511603,3-dimethyl-N-[3-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidin-2-yl]butanamide

Product 1

HCID 68750743N-{3-[(E)-2-(4-chlorophenyl)vinyl]pyrazolo[1,5-a]pyrimidin-2-yl}-3,3-dimethylbutanamide

Procedure

The product from Example 110B and trans-2-(4-chlorophenyl)vinylboronic acid were processed using the method analogous to that described in Example 110C to afford the title compound. H NMR (400 MHz, CD3OD) δ ppm 8.80 (dd, J=7.0, 1.7 Hz, 1H), 8.60 (dd, J=4.1, 1.6 Hz, 1H), 7.65 (d, J=16.3 Hz, 1H), 7.47-7.50 (m, 2H), 7.31-7.34 (m, 2H), 7.19 (d, J=16.5 Hz, 1H), 7.03 (dd, J=7.0, 4.1 Hz, 1H), 2.41-2.41 (bs, 2H), 1.17 (s, 9H); MS (ESI) m/z 369 (M+H)+.

Sources & evidence

ORD record
ord-ffe95588bb4a46ccb5ab8f250fa30b02
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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