Sodium Nitrite → HCID 58015551, compound

HRID 422081Notes

Reaction equation

[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:17]=[CH:16][C:15]3[O:18][C:19]([Br:21])=[CH:20][C:14]=3[C:13]2=[O:22])=[CH:8][C:7]=1[CH3:23]>CC(O)=O.O>[Br:21][C:19]1[O:18][C:15]2[CH:16]=[CH:17][N:12]([C:9]3[CH:8]=[C:7]4[C:6](=[CH:11][CH:10]=3)[NH:5][N:1]=[CH:23]4)[C:13](=[O:22])[C:14]=2[CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

NaNO2 (174 mg, 2.52 mmol) was added to a solution of crude 5-(4-amino-3-methylphenyl)-2-bromofuro[3,2-c]pyridin-4(5H)-one (800 mg, 2.52 mmol) in 5:1 AcOH/H2O (24 mL) and the resulting solution was stirred at 25° C. for 14 h. The solution was concentrated under reduced pressure. Flash chromatography on silica gel (49:1 CH2Cl2/MeOH) afforded the title compound (373 mg, 44%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 13.30-13.25 (br s, 1H, NH), 8.16 (s, 1H), 7.81 (d, J=1.8 Hz, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.35 (dd, J=8.7, 1.8 Hz, 1H), 7.19 (d, J=0.6 Hz, 1H), 6.85 (dd, J=7.5, 0.6 Hz, 1H).

Workup

concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0db9bbc71ac048c1b6153734d6d77fb2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101632B2

Reaction notes

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