4-Bromoaniline → HCID 86702086, compound

HRID 715793Notes

Reaction equation

HRID 715793 reaction equation
[CH3:1][C:2]1(C)C(C)(C)OB(C2C=NNC=2)[O:3]1.[CH2:15]([N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1)[CH:16]([CH3:18])[CH3:17].Br[C:34]1[S:38][C:37]([C:39]([NH:41][CH2:42][C:43]2[CH:48]=[CH:47][N:46]3[CH:49]=[CH:50][N:51]=[C:45]3[CH:44]=2)=[O:40])=[CH:36][CH:35]=1.Br[C:53]1C=CC(N)=CC=1>>[N:51]1[CH:50]=[CH:49][N:46]2[CH:47]=[CH:48][C:43]([CH2:42][NH:41][C:39]([C:37]3[S:38][C:34]([C:22]4[CH:21]=[N:20][N:19]([CH2:15][C:16]5([CH3:17])[CH2:18][CH2:53][O:3][CH2:2][CH2:1]5)[CH:23]=4)=[CH:35][CH:36]=3)=[O:40])=[CH:44][C:45]=12

Participants

5

Reactant 4

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867019355-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide

Product 1

HCID 86702086HCID 86702086, compound

Procedure

The title compound was prepared as described in Example 51A, substituting 14(4-methyltetrahydro-2H-pyran-4-yl)methyl)-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)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.1, 1.0 Hz, 1H), 8.13 (s, 1H), 7.89 (t, J=1.0 Hz, 1H), 7.81 (s, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.3 Hz, 1H), 7.43-7.36 (m, 1H), 7.23 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.1, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.8, 4.6 Hz, 2H), 3.52 (ddd, J=11.9, 9.1, 3.0 Hz, 2H), 1.51 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.24 (dt, J=13.4, 4.0 Hz, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 436 (M+H)+.

Sources & evidence

ORD record
ord-216c94520c4d4e528614750b02300036
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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