Potassium Carbonate → HCID 46199380, compound

HRID 1966476Notes

Reaction equation

[C:1]1([NH:7][C:8]2[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)([OH:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.C(OCC)(=O)C>[N+:15]([C:9]1[CH:10]=[CH:11][C:12]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:18]([OH:20])=[O:19])[CH:26]=2)=[CH:13][C:8]=1[NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-Phenyl-5-bromo-2-nitrobenzenamine (0.9 g, 3.2 mmol) and 3-carboxyphenylboronic acid (0.64 g, 3.92 mmol) in Toluene: EtOH: H2O (8:8:1) was added K2CO3 (1.4 g, 9.78 mmol). After stirring reaction for 15 min under argon tetrakis (triphenylphosphine) palladium (0.184 mg, 0.016 mol) was added, resulting mixture was then heated at 100° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and extracted three times with water. The aqueous layer was then acidified with 2M HCl to get 4′-nitro-3′-(phenylamino) biphenyl-3-carboxylic acid (0.8. g), 84% yield. 1H NMR (500 MHz, DMSO): δ 7.23 (m, 2H), 7.44 (m, 4H), 7.61 (t, J=7.7 Hz, 1H), 7.83 (d, J=7.7 Hz, 1H), 8.00 (d, J=7.7 Hz 1H), 8.07 (s, 1H), 8.25 (d, J=9 Hz, 1H), 9.50 (s, 1H), 13.15 (bs, 1H). HRMS (ESI) calculated for C19H14N2NaO4: 357.0846, Found: 357.0816.

Workup

customreaction for 15 min under argon tetrakis (triphenylphosphine) palladium (0.184 mg, 0.016 mol)
additionwas added
customresulting mixture
temperatureThe reaction mixture was cooled to room temperature
extractionextracted three times with water

Sources & evidence

ORD record: ord-136d54e28b2d4640b6f64ab70940e31b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420640B2

Reaction notes

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