4-Bromoaniline → HCID 86702091, compound

HRID 715832Notes

Reaction equation

HRID 715832 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](C)C.Br[C:20]1[CH:38]=[CH:37][C:23]([C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][N:31]3[CH:34]=[CH:35][N:36]=[C:30]3[CH:29]=2)=[O:25])=[CH:22][CH:21]=1.Br[C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=C[CH:41]=1>>[N:36]1[CH:35]=[CH:34][N:31]2[CH:32]=[CH:33][C:28]([CH2:27][NH:26][C:24](=[O:25])[C:23]3[CH:37]=[CH:38][C:20]([C:46]4[CH2:45][CH2:43][N:44]([C:7]5[CH:8]=[CH:9][N:5]=[C:1]([CH3:2])[N:6]=5)[CH2:41][CH:40]=4)=[CH:21][CH:22]=3)=[CH:29][C:30]=12

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86702090HCID 86702090, compound

Product 1

HCID 86702091HCID 86702091, compound

Procedure

The title compound was prepared as described in Example 51A, substituting 2-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl)pyrimidine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07-8.95 (m, 1H), 8.78 (dd, J=7.0, 0.5 Hz, 1H), 8.28-8.16 (m, 2H), 8.00 (d, J=2.0 Hz, 1H), 7.97-7.87 (m, 2H), 7.80-7.74 (m, 1H), 7.63-7.54 (m, 2H), 7.40 (dd, J=7.0, 1.5 Hz, 1H), 7.04 (d, J=7.4 Hz, 1H), 6.41-6.31 (m, 1H), 4.66 (m, 2H), 4.47 (m, 2H), 4.10 (t, J=5.8 Hz, 2H), 2.77-2.64 (m, 2H), 2.55 (s, 3H); MS (ESI(+)) m/e 425 (M+H)+.

Sources & evidence

ORD record
ord-c10d1eb0c08d46c9951ebb1eccf5ca9b
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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