1,2-Dichloroethane → 2-bromo-N-(4'-chloro-[1,1'-biphenyl]-4-yl)-4-methylbenzamide

HRID 405220Notes

Reaction equation

HRID 405220 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Br:15][C:16]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18]([NH:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:19]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 86754-Amino-4'-chlorodiphenylHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2262922-Bromo-4-methylbenzoic acid

Product 1

HCID 710600832-bromo-N-(4'-chloro-[1,1'-biphenyl]-4-yl)-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-chloro-[1,1′-biphenyl]-4-amine (159 mg, 0.78 mmol), 2-bromo-4-methylbenzoic acid (140 mg, 0.65 mmol), EDC (125 mg, 0.65 mmol), HOBt (100 mg, 0.65 mmol), and diisopropylethyl amine (0.22 mL, 1.30 mmol) were dissolved in THF (2.6 mL) and stirred at room temperature. After 3 h the resulting mixture directly purified via column chromatography to yield the title compound.

Workup

  1. customAfter 3 h the resulting mixture directly purified via column chromatography

Sources & evidence

ORD record
ord-5c7d59f64ce94b76a6e62c06cf8ab6b8
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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