3-(Trifluoromethyl)phenol → HCID 23502796, compound

HRID 1835359Notes

Reaction equation

HRID 1835359 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8](=[O:24])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([CH2:22][OH:23])=[N:11][CH:10]=1.O[C:36]1[CH:37]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:40][CH:41]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[F:31][C:29]([F:32])([F:30])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:33])([F:1])[F:34])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8](=[O:24])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([CH2:22][O:23][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=2)=[N:11][CH:10]=1

Participants

7

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10299574HCID 10299574, compound

Product 1

HCID 23502796HCID 23502796, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 80 mg (0.17 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-hydroxymethyl-N-methyl-4-o-tolyl-nicotinamide (Example 7), 0.027 ml (0.22 mmol) 3-hydroxybenzotrifluoride, 47 mg (0.17 mmol) triphenylphosphine and 32 mg (0.17 mmol) diethyl azodicarboxylate in 2 ml tetrahydrofuran was stirred at room temperature over night. The reaction mixture was diluted with ethyl acetate and washed with 1N aqueous sodium hydroxide solution. The aqueous layer was extracted with three portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 62 mg (60%) of the title compound as a light yellow amorphous mass.

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution
  2. extractionThe aqueous layer was extracted with three portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab79a4dde9e243bd9c02ce13e5667d18
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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