2,2,2-Trifluoroethanol → HCID 86705950, compound

HRID 625329Notes

Reaction equation

HRID 625329 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[F:9][C:10]([F:38])([F:37])[C:11]1[CH:12]=[C:13]([CH:34]=[CH:35][CH:36]=1)[CH2:14][NH:15][C:16](=[O:33])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]2[CH:28]=[C:27](F)[CH:26]=[CH:25][C:24]=2[N+:30]([O-:32])=[O:31])[CH:18]=1>O1CCCC1.O>[F:37][C:10]([F:9])([F:38])[C:11]1[CH:12]=[C:13]([CH:34]=[CH:35][CH:36]=1)[CH2:14][NH:15][C:16](=[O:33])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]2[CH:28]=[C:27]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:26]=[CH:25][C:24]=2[N+:30]([O-:32])=[O:31])[CH:18]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 66586802N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)-isonicotinamide

Product 1

HCID 86705950HCID 86705950, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 2,2,2-trifluoroethanol (150 mg, 1.50 mmol, 2.00 equiv) in tetrahydrofuran (10 mL). This was followed by the addition of sodium hydride (180 mg, 7.50 mmol, 10.00 equiv), in portions at 0° C. The resulting solution was stirred for 20 min at 0° C. in an ice/salt bath. To this was added N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide 14d (300 mg, 0.72 mmol, 1.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 20 mL of water. The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined and dried over sodium sulfate and concentrated under vacuum. This resulted in 200 mg (crude) of N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(2,2,2-trifluoroethoxy)phenyl)isonicotinamide as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 200 mg (crude) of N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(2,2,2-trifluoroethoxy)phenyl)isonicotinamide as a yellow solid

Sources & evidence

ORD record
ord-42270cdae1414d2c9055a95f0894bd79
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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