Tributylphosphine → {4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester

HRID 2261848Notes

Reaction equation

HRID 2261848 reaction equation
C(P(CCCC)CCCC)CCC.N1CCCCC1.N1CCCCC1.N(C(O)=O)=NC(O)=O.[CH:34]1([C:37]2[CH:41]=[N:40][N:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[O:48][C:49]([F:52])([F:51])[F:50])[C:38]=2[CH2:53][OH:54])[CH2:36][CH2:35]1.[C:55]([O:59][C:60](=[O:70])[NH:61][C:62]1[CH:67]=[CH:66][C:65](O)=[CH:64][C:63]=1[CH3:69])([CH3:58])([CH3:57])[CH3:56]>C1(C)C=CC=CC=1>[C:55]([O:59][C:60](=[O:70])[NH:61][C:62]1[CH:67]=[CH:66][C:65]([O:54][CH2:53][C:38]2[N:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[O:48][C:49]([F:52])([F:50])[F:51])[N:40]=[CH:41][C:37]=2[CH:34]2[CH2:35][CH2:36]2)=[CH:64][C:63]=1[CH3:69])([CH3:58])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 13831Tributylphosphine2×HCID 15429162tert-Butyl (4-hydroxy-2-methylphenyl)carbamateHCID 57443267[4-cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanolHCID 66707187Azodicarboxylate dipiperidine

Product 1

HCID 57443358{4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tri-n-butylphosphine (1.9 mL, 7.5 mmol) and azodicarboxylic acid dipiperidine (1.90 g, 7.54 mmol) are added to a mixture of [4-cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanol (1.50 g, 5.03 mmol), (4-hydroxy-2-methyl-phenyl)-carbamic acid tert-butyl ester (1.35 g, 6.03 mmol) and toluene at room temperature. After 1 h, additional tri-n-butylphosphine (0.6 mL) is added and the mixture is stirred for 2 h. The mixture is concentrated and the residue is purified by flash chromatography (20 to 50% EtOAc/heptane) to give the title compound (1.92 g, 76%). LC-ES/MS m/e 504.2 (M+1).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is purified by flash chromatography (20 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-978edd980f9546e7b942be1307c852c3
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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