4-Bromo-2-nitroaniline → HCID 22478116, compound

HRID 2182406Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:17][C:16]1[CH:18]=[CH:19][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

Conditions

Temperature: 85 °C

Procedure

A stirred solution of 3-cyanophenyl boronic acid (812 mg) and tetrakis(triphenylphosphine) palladium (150 mg) in tetrahydrofuran (4 mL) under at atmosphere of nitrogen was treated with 4-bromo-2-nitroaniline in tetrahydrofuran (10 mL). The reaction mixture was heated at 85° C. for 48 hours, then cooled to ambient temperature and then partitioned between ethyl acetate and water. The organic layer was washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to give 4′-amino-3′-nitro-biphenyl-3-carbonitrile (224 mg) as a yellow solid. LC-MS (METHOD B): RT=3.21 minutes, 240.3 (M+H)+. (b) 2-nitro-4-pyridine-3-yl-phenylamine

Workup

temperaturecooled to ambient temperature
custompartitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated
additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

Sources & evidence

ORD record: ord-12435d12e3bf48c9be844126ca2e7c21
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897208B2

Reaction notes

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