Toluene → HCID 118161858, compound

HRID 1482868Notes

Reaction equation

HRID 1482868 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1.[F:22][C:23]([F:42])([F:41])[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]3[O:38][N:37]=[C:36]([OH:39])[C:35]=3[CH:40]=2)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:62][N:63]1[CH:67]=[C:66]([CH2:68]O)[N:65]=[CH:64]1>C1COCC1>[CH3:62][N:63]1[CH:67]=[C:66]([CH2:68][O:39][C:36]2[C:35]3[CH:40]=[C:31]([C:28]4[CH:29]=[CH:30][C:25]([O:24][C:23]([F:22])([F:41])[F:42])=[CH:26][CH:27]=4)[CH:32]=[CH:33][C:34]=3[O:38][N:37]=2)[N:65]=[CH:64]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 7060524(1-methyl-1H-imidazol-4-yl)methanolHCID 178518982HCID 178518982, compound

Product 1

HCID 118161858HCID 118161858, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate 40% solution in toluene (0.27 mL, 0.51 mmol) was added under stirring to a solution of 5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-ol (100 mg, 0.34 mmol), triphenylphosphine on resin (3 mmol/g) (330 mg, 1 mmol), and 1-methylimidazol-4-yl methanol (60 mg, 0.51 mmol) in THF. The reaction mixture was stirred at ambient temperature overnight. Volatiles were evaporated under vacuum and the residue was purified on 12 g silica gel with 0-20% methanol in dichloromethane and gave the title compound (40 mg, 0.103 mmol) as yellowish oil.

Workup

  1. customVolatiles were evaporated under vacuum
  2. customthe residue was purified on 12 g silica gel with 0-20% methanol in dichloromethane

Sources & evidence

ORD record
ord-776e0eddcccb43e08b4ff2cf870fa24b
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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