1,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-ol → 2-{4-[(5-Chloro-benzo[b]thiophen-2-ylmethyl)-(2,2,2-trifluoro-ethyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

HRID 599801Notes

Reaction equation

HRID 599801 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[Cl:23][C:24]1[CH:34]=[CH:33][C:27]2[S:28][C:29]([CH2:31]Cl)=[CH:30][C:26]=2[CH:25]=1>CC(O)(C)C>[Cl:23][C:24]1[CH:34]=[CH:33][C:27]2[S:28][C:29]([CH2:31][N:15]([CH2:16][C:17]([F:19])([F:18])[F:20])[C:12]3[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:21])([F:22])[F:1])=[CH:14][CH:13]=3)=[CH:30][C:26]=2[CH:25]=1

Participants

4

Reactant 2

HCID 4479111,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-olHCID 151337565-Chloro-2-chloromethyl-benzo[b]thiophene

Product 1

HCID 115337382-{4-[(5-Chloro-benzo[b]thiophen-2-ylmethyl)-(2,2,2-trifluoro-ethyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-olYield 19.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 100 mg (0.29 mmol) of 1,1,1,3,3,3-hexafluoro-2-[4-(2,2,2-trifluoro-ethylamino)-phenyl]-propan-2-ol (example 11.2) in 0.5 mL tBuOH was treated with 115 mg (0.44 mmol) of 5-chloro-2-chloromethyl-benzo[b]thiophene and stirred at 120° C. for 10 hours in a sealed tube. Evaporation of the solvent and column chromatography on silicagel with n-heptane/EtOAc 8:1 yielded 30 mg (19%) of 2-{4-[(5-chloro-benzo[b]thiophen-2-ylmethyl)-(2,2,2-trifluoro-ethyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow oil, MS: 520 ((M-H)−, 1Cl).

Workup

  1. customEvaporation of the solvent and column chromatography on silicagel with n-heptane/EtOAc 8:1

Sources & evidence

ORD record
ord-76df2dc4e67b4f7f9a9cc7afc81956c4
Source dataset
uspto-grants-2011_03
Patent number
US07897815B2

Reaction notes

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