Triphenylphosphine → ethyl 3-[4-({4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoate

HRID 2110912Notes

Reaction equation

HRID 2110912 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:31]=[C:30](O)[CH:29]=[CH:28][C:27]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][O:24][C:30]3[CH:29]=[CH:28][C:27]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:26]([F:25])[CH:31]=3)=[CH:21][CH:22]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 23157326{4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol

Product 1

HCID 23159891ethyl 3-[4-({4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of {4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol (320 mg, 1.0 mmol), ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (212 mg, 1.0 mmol), triphenylphosphine (262 mg, 1.0 mmol) and dichloromethane (5 mL) added dropwise diethyl azodicarboxylate (40% toluene solution, 435 mg, 1.0 mmol) with stirring at room temperature, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2) to give the title compound as a yellow oil. 1H NMR (CDCl3) δ: 1.26 (3H, t, J=7.2 Hz), 1.37 (9H, s), 2.58 (2H, t, J=7.6 Hz), 2.90 (2H, t, J=7.6 Hz), 4.12 (2H, q, J=7.2 Hz), 4.97 (2H, s), 5.32 (2H, s), 6.20 (1H, s), 6.60-6.70 (2H, m), 7.02 (2H, d, J=8.1 Hz), 7.09 (1H, t, J=8.8 Hz), 7.25-7.40 (7H, m).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customAfter completion of the reaction
  3. customthe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2)

Sources & evidence

ORD record
ord-32469f0f06c44ca5a15eb3763ecb4a56
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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