alpha-Bromo-o-chlorotoluene → HCID 44205297, compound

HRID 1029289Notes

Reaction equation

HRID 1029289 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][CH:22]=[CH:21][C:20]=1[Cl:25]>>[Cl:25][C:20]1[CH:21]=[CH:22][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 11905alpha-Bromo-o-chlorotolueneHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 44205297HCID 44205297, compoundYield 6.3%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (139 mg, 0.66 mmol) and 1-(bromo-methyl)-2-chlorobenzene (162 mg, 0.79 mmol) to provide 470 (14 mg, 6% yield) as a white powder. LC-MS (M+H=337, obsd.=337). 1H NMR (400 MHz, DMSO-D6) δ 11.51 (s, 1H), 8.56 (d, J=6.8, 1H), 8.42 (dd, J=1.6, 4.7, 1H), 8.01 (d, J=8.8, 1H), 7.44 (m, 2H), 7.39 (d, J=2.1, 1H), 7.29 (m, 2H), 7.18 (m, 2H), 6.95 (dd, J=2.1, 8.8, 1H), 4.58 (d, J=5.9, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-0e00d29953e64c9794af06cbeb42651a
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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