2,4-Bis(trifluoromethyl)benzyl bromide → HCID 58168202, compound

HRID 1029276Notes

Reaction equation

HRID 1029276 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[C:29]([F:32])([F:31])[F:30]>>[F:30][C:29]([F:31])([F:32])[C:20]1[CH:21]=[C:22]([C:25]([F:28])([F:26])[F:27])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3

Participants

3

Reactant 2

HCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168202HCID 58168202, compoundYield 22.1%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 454 using 70 (121 mg, 0.57 mmol) and 1-(bromo-methyl)-2,4-bis(trifluoromethyl)benzene (176 mg, 0.57 mmol) to provide 455 (55 mg, 22% yield) as a white powder. LC-MS (M+H=438, obsd.=438). 1H NMR (400 MHz, DMSO-D6) δ 11.55 (s, 1H), 8.37 (m, 2H), 8.06 (dd, J=7.9, 13.0, 2H), 7.84 (d, J=8.5, 1H), 7.31 (m, 2H), 7.24 (dd, J=4.7, 7.9, 1H), 6.94 (dd, J=2.1, 8.8, 1H), 4.77 (d, J=5.7, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-6fd816b332d04730b9c94877b28c0841
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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