4-Bromoaniline → HCID 86701988, compound

HRID 717966Notes

Reaction equation

HRID 717966 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3].Br[C:20]1[O:24][C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][N:32]3[CH:35]=[CH:36][N:37]=[C:31]3[CH:30]=2)=[O:26])=[CH:22][CH:21]=1.Br[C:39]1[CH:45]=CC(N)=C[CH:40]=1>>[CH2:1]([N:5]1[CH:9]=[C:8]([C:20]2[O:24][C:23]([C:25]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][N:32]4[CH:35]=[CH:36][N:37]=[C:31]4[CH:30]=3)=[O:26])=[CH:22][CH:21]=2)[CH:7]=[N:6]1)[C:2]1[CH:3]=[CH:45][CH:39]=[CH:40][CH:4]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86701989HCID 86701989, compound

Product 1

HCID 86701988HCID 86701988, compound

Procedure

The title compound was prepared as described in Example 51A, substituting 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) ppm 8.92 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.27 (d, J=0.7 Hz, 1H), 7.93 (d, J=0.7 Hz, 1H), 7.89 (t, J=0.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.23 (m, 6H), 7.17 (d, J=3.5 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 5.39 (s, 2H), 4.49 (d, J=6.1 Hz, 2H); MS (ESI(+)) m/e 398 (M+H)+.

Sources & evidence

ORD record
ord-d5b80cc21a2b4e9aa46d405f93e2dbf0
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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