4-Bromoaniline → HCID 86702004, compound

HRID 717977Notes

Reaction equation

HRID 717977 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]1C=CC(N)=CC=1>>[CH3:39][C:2]([CH3:3])([CH3:4])[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

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 86702004HCID 86702004, compound

Procedure

The title compound was prepared as described in Example 51A, substituting 1-neopentyl-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 (300 MHz, DMSO-d6) δ ppm 8.89 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.11 (d, J=0.5 Hz, 1H), 7.95-7.83 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.46-7.34 (m, 1H), 7.17 (d, J=3.4 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.66 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 3.95 (s, 2H), 0.92 (s, 9H); MS (ESI(+)) m/e 378 (M+H)+.

Sources & evidence

ORD record
ord-a5ae43af406d45dd82727a729b8bc7b3
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

Loading…