alpha-Bromo-2-nitrotoluene → HCID 58168154, compound

HRID 1029286Notes

Reaction equation

HRID 1029286 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.[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][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)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 77569alpha-Bromo-2-nitrotolueneHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168154HCID 58168154, compoundYield 12.2%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (121 mg, 0.57 mmol) and 2-nitro-benzyl bromide (118 mg, 0.69 mmol) to provide 466 (24 mg, 12% yield) as a white powder. LC-MS (M+H=347, obsd.=347). 1H NMR (400 MHz, DMSO-D6) δ 8.56 (d, J=6.6, 1H), 8.41 (d, J=3.1, 1H), 8.07 (dd, J=8.3, 15.1, 2H), 7.51 (dt, J=6.5, 14.0, 2H), 7.43 (d, J=1.9, 1H), 7.35 (dd, J=4.7, 7.9, 1H), 7.03 (d, J=7.6, 1H), 6.91 (dd, J=2.0, 8.7, 1H), 6.25 (s, 2H), 5.89 (s, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-cefed1445d8045d4996ab07a5da45b69
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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