1,2-Dichloroethane → Methyl 2'-(((2,4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 2167147Notes

Reaction equation

HRID 2167147 reaction equation
ClCCCl.[CH:5]([C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1)=O.[Cl:29][C:30]1[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:31]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1>C(Cl)Cl>[Cl:29][C:30]1[CH:35]=[C:34]([NH:36][CH2:5][C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]([F:16])([F:17])[F:18])=[CH:9][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[CH:33]=[CH:32][C:31]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 198789103-Chloro-4-(4-chlorophenyl)benzenamineHCID 86674212Methyl 2'-formyl-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 71059990Methyl 2'-(((2,4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid NaBH(Oac)3 (113 mg, 0.54 mmol) was added to a DCE solution (4 mL) of methyl 2′-formyl-3′-methoxy-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylate (121 mg, 0.36 mmol) and 2,4′-dichloro-[1,1′-biphenyl]-4-amine (93 mg, 0.39 mmol), and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was diluted with DCM, washed with saturated aqueous NaHCO3 and water, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3 and water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-25e58d3df4c943e6932f2a445852d51d
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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