4-Bromoaniline → HCID 11295314, compound

HRID 28610Notes

Reaction equation

HRID 28610 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[C:6]([C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:12]2[CH:13]=[C:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:9]=[C:10]([NH2:15])[N:11]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 860043644-[5-Bromo-2-(2,2,2-trifluoro-ethoxy)-phenyl]-6-chloro-pyrimidin-2-ylamine

Product 1

HCID 11295314HCID 11295314, compoundYield 34%

Procedure

Following the method described in Example 26, 4-[5-bromo-2-(2,2,2-trifluoro-ethoxy)-phenyl]-6-chloro-pyrimidin-2-ylamine and 4-bromo-phenylamine provided the title compound (34% yield). 1H NMR (acetone-d6) δ 4.76 (q, 2H, J=8.5 Hz, CH2), 5.95 (bs, 2H, NH2), 6.72 (s, 1H, Ar), 7.21 (d, 1H, J=8.8 Hz, Ar), 7.44 (d, 2H, J=8.9 Hz, Ar), 7.58 (dd, 1H, J=8.8 Hz, J=2.4 Hz, Ar), 7.75-7.78 (m, 2H, Ar), 8.07 (d, 1H, J=2.4 Hz, Ar), 8.62 (br s, 1H, NH).

Sources & evidence

ORD record
ord-9d13933a8ed24dec928c573897811012
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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