Triethylamine → 4-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenylamino}-benzoic acid methyl ester

HRID 1095916Notes

Reaction equation

HRID 1095916 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:42])[C:29]([C:35]2[CH:40]=[CH:39][N:38]=[C:37]([Cl:41])[CH:36]=2)([OH:34])[C:30]([F:33])([F:32])[F:31])=[C:24]([Cl:43])[CH:23]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:42])[C:29]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([Cl:41])[CH:36]=3)([OH:34])[C:30]([F:31])([F:32])[F:33])=[C:24]([Cl:43])[CH:23]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 866459524-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenylamino}-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II)acetate (60 mg), (4-methoxycarbonylphenyl)boronic acid (CAS Reg. No. 99768-12-4, 59 mg), and triethylamine (44 mg) were added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 68 step 4, 40 mg) in DCM (4 ml). The mixture was stirred with molecular sieves under air atmosphere for 18 h and then concentrated to an oil. The residue was purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (10 mg) as a white foam. MS (m/e)=499.1 [M+H+].

Workup

  1. concentrationconcentrated to an oil
  2. customThe residue was purified by prep

Sources & evidence

ORD record
ord-4b391a1e2f094ce6907f954592d99a8e
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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