4-Bromoaniline → HCID 86702087, compound

HRID 715823Notes

Reaction equation

HRID 715823 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[N:44]=[CH:45][C:46]3[N:47]([CH:49]=[CH:50][N:51]=3)[CH:48]=2)=[O:40])=[CH:36][CH:35]=1.Br[C:53]1C=CC(N)=CC=1>>[N:51]1[CH:50]=[CH:49][N:47]2[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])[N:44]=[CH:45][C:46]=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 86702088HCID 86702088, compound

Product 1

HCID 86702087HCID 86702087, 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]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.09-9.01 (m, 2H), 8.53 (d, J=1.4 Hz, 1H), 8.18-8.15 (m, 1H), 8.13 (d, J=0.5 Hz, 1H), 7.83-7.79 (m, 2H), 7.76 (d, J=3.9 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.4, 4.5 Hz, 2H), 3.51 (ddd, J=11.8, 9.2, 2.9 Hz, 2H), 1.50 (ddd, J=13.4, 9.1, 4.1 Hz, 2H), 1.33-1.18 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 437 (M+H)+.

Sources & evidence

ORD record
ord-8da83cf4551b4012a02fd8903b54a52a
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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