Sodium Iodide → 1,1,1,3,3,3-Hexafluoro-2-(4-(((5-methyl-2-(3-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)(2,2,2-trifluoroethyl)amino)phenyl)propan-2-ol

HRID 599809Notes

Reaction equation

HRID 599809 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[CH2:24][C:25]1[N:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[O:28][C:29]=1[CH3:30].[Na+].[I-].[NH4+].[Cl-]>CN(C=O)C.CCOCC>[F:1][C:2]([F:21])([F:22])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH2:24][C:25]2[N:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[O:28][C:29]=2[CH3:30])[CH2:16][C:17]([F:19])([F:18])[F:20])=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 25517Ammonium ChlorideHCID 4479111,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-olHCID 105884614-Chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazole

Product 1

HCID 115923041,1,1,3,3,3-Hexafluoro-2-(4-(((5-methyl-2-(3-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)(2,2,2-trifluoroethyl)amino)phenyl)propan-2-olYield 1.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture 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), of 81 mg (0.29 mmol) 4-chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazole and ca 10 mg of NaI in DMF was stirred for 1 week at 125° C. and then distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with a gradient of n-heptane/EtOAc gave 2 mg (ca. 1%) of 1,1,1,3,3,3-hexafluoro-2-{4-[[5-methyl-2-(3-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-(2,2,2-trifluoro-ethyl)-amino]-phenyl}-propan-2-ol, yellow solid, MS: 581 (MH+).

Workup

  1. dry with materialDrying of the combined organic phases over Na2SO4 and column chromatography on silica gel with a gradient of n-heptane/EtOAc

Sources & evidence

ORD record
ord-fc14848b73b843bd8c4d7785ea1dd8e5
Source dataset
uspto-grants-2011_03
Patent number
US07897815B2

Reaction notes

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