4-Bromoaniline → HCID 86702071, compound

HRID 873584Notes

Reaction equation

HRID 873584 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[CH:25]=[CH:24][C:23]([NH:26][C:27]([CH:29]2[CH2:32][N:31]([C:33]3[N:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[CH2:30]2)=[O:28])=[CH:22][CH:21]=1.Br[C:40]1C=CC(N)=CC=1>>[CH3:40][C:2]([CH3:3])([CH3:4])[CH2:1][N:5]1[CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([CH:29]3[CH2:32][N:31]([C:33]4[N:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[CH2:30]3)=[O:28])=[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 86702072HCID 86702072, compound

Product 1

HCID 86702071HCID 86702071, compound

Procedure

The title compound was prepared as described in Example 148A, 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 N-(4-bromophenyl)-1-(pyridazin-3-yl)azetidine-3-carboxamide for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.14 (s, 1H), 8.57 (dd, J=4.5, 1.2 Hz, 1H), 8.05 (s, 1H), 7.82 (s, 1H), 7.66-7.58 (m, 2H), 7.55-7.51 (m, 2H), 7.48 (dd, J=9.1, 4.5 Hz, 1H), 6.98 (dd, J=9.1, 1.1 Hz, 1H), 4.30 (t, J=8.6 Hz, 2H), 4.22 (dd, J=8.4, 6.0 Hz, 2H), 3.90 (s, 2H), 3.77 (tt, J=8.6, 5.9 Hz, 1H), 0.92 (s, 9H); MS (ESI(+)) m/e 391 (M+H)+.

Sources & evidence

ORD record
ord-ec455a2f206544878c0a71989b2a6b17
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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