Water → 2-Fluoro-5-nitro-[1,1';4'1'']terphenyl-4-ylamine

HRID 1960130Notes

Reaction equation

[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[F:22][C:23]1[C:24](I)=[CH:25][C:26]([N+:30]([O-:32])=[O:31])=[C:27]([NH2:29])[CH:28]=1.O>C1(C)C=CC=CC=1.CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:23]1[CH:28]=[C:27]([NH2:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][C:24]=1[C:13]1[CH:14]=[CH:15][C:10]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-Biphenylboronic acid (737 mg, 2.4 mmol), K2CO3 (995 mg, 7.2 mmol), Pd(PPh3)4 (139 mg, 0.12 mmol), compound 13-1 (700 mg, 2.4 mmol) in 10 mL toluene, 2 mL DMF, and 2 mL H2O was suspended in a microwave reactor vial and heated to 130° C. for 10 min in a microwave reactor. The resulting dark solution was then diluted with EtOAc (150 mL) and washed three times with 50 mL portions of saturated aqueous NH4Cl. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The crude product was purified on ISCO (EtOAc/Hexanes=6/4) to give title compound 13-2.

Workup

customwas suspended in a microwave reactor
washwashed three times with 50 mL portions of saturated aqueous NH4Cl
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified on ISCO (EtOAc/Hexanes=6/4)

Sources & evidence

ORD record: ord-6eb49e05e5064b598da627267f7afe8a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410284B2

Reaction notes

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