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

HRID 1960130
Notes
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Reaction equation

HRID 1960130 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 574814875-Fluoro-4-iodo-2-nitrobenzenamine

Product 1

HCID 674465092-Fluoro-5-nitro-[1,1';4'1'']terphenyl-4-ylamine

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

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

  1. customwas suspended in a microwave reactor
  2. washwashed three times with 50 mL portions of saturated aqueous NH4Cl
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes