Sodium Hydroxide → 3-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

HRID 1095911Notes

Reaction equation

HRID 1095911 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8](CC=C)CC=C)[CH:5]=[CH:4][C:3]=1[CH:15]([CH3:29])[C:16]([C:22]1[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[CH:23]=1)([OH:21])[C:17]([F:20])([F:19])[F:18].[OH-].[Na+]>C(Cl)Cl.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>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:15]([CH3:29])[C:16]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[CH:23]=2)([OH:21])[C:17]([F:18])([F:19])[F:20])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 574212893-(2-Chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-olYield 69.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-dimethylbarbituric acid (420 mg) and Pd(PPh3)4 (117 mg) were added to a solution of 3-(2-chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (300 mg) in DCM (60 ml). The mixture was heated under reflux for 3 h. 1N aqueous NaOH solution was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 50% EtOAc/heptane) to give the title compound (170 mg) as light yellow foam. MS (m/e)=365.0 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, 0 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-87cb7f92900a4270a6a081acd1a5112c
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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