Triethylamine → HCID 86645953, compound

HRID 1095917Notes

Reaction equation

HRID 1095917 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.[Cl:21][C:22]1[CH:23]=[C:24]([OH:43])[CH:25]=[CH:26][C:27]=1[CH:28]([CH3:42])[C:29]([C:35]1[CH:40]=[CH:39][N:38]=[C:37]([Cl:41])[CH:36]=1)([OH:34])[C:30]([F:33])([F:32])[F:31]>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]([O:43][C:24]2[CH:25]=[CH:26][C:27]([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:22]([Cl:21])[CH:23]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 574212643-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol

Product 1

HCID 86645953HCID 86645953, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II)acetate (30 mg), (4-methoxycarbonylphenyl)boronic acid (CAS Reg. No. 99768-12-4, 30 mg), and triethylamine (22 mg) were added to a solution of 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol (Example 19 step 5, 20 mg) in DCM (2 ml). The mixture was stirred with molecular sieves under air atmosphere overnight 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 (15 mg) as a white solid. MS (m/e)=500.1 [M+H+].

Workup

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

Sources & evidence

ORD record
ord-1f6d37f56fe040bea3a893eaf029fbec
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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