Triphenylphosphine → HCID 67131198, compound

HRID 1678659Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:18][OH:19])=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][O:27][C:28](=[O:38])[C:29]1[CH:34]=[C:33]([CH3:35])[C:32](O)=[C:31]([CH3:37])[CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:26][O:27][C:28](=[O:38])[C:29]1[CH:30]=[C:31]([CH3:37])[C:32]([O:19][CH2:18][CH:17]([C:16]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[C:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:33]([CH3:35])[CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-2-cyclohexyl-ethanol (20 mg, 56 umol) in THF (1 ml) was added 4-hydroxy-3,5-dimethyl-benzoic acid methyl ester (11 mg, 62 umol; CAS Reg. No. 34137-14-9) and tri-phenylphosphine (18 mg, 68 umol) at ambient temperature under an argon atmosphere. The mixture was cooled to 0° C., di-tert-butyl azodicarboxylate (16 mg, 68 umol) was added and the suspension was stirred for 14 h at ambient temperature. The solvent was removed under reduced pressure to give a solid which was purified by column chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (8 mg, 15 umol; 27%) as colorless oil. MS: m/e=517.3 [M+H+].

Workup

customat ambient temperature
customThe solvent was removed under reduced pressure
customto give a solid which
customwas purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record: ord-a54cd12794a440aaa6c31c1d9b2a1afd
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008505B2

Reaction notes

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