Phenol → HCID 46184685, compound

HRID 417089Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[C:28]1(O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:14][O:15][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.2 g (0.51 mmol) 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, int. c) in 4 mL tetrahydrofuran were added 53 mg (0.56 mmol) phenol and 124 mg (0.61 mmol) tri-n-butylphosphin. The reaction mixture was cooled down to 0° C. and 106 mg (0.61 mmol) N,N,N′,N′-tetramethylazodicarboxamide were added. After stirring for 18 h at room temperature the reaction mixture was evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) with a gradient of n-heptane:Ethyl acetate (100:0 to 60:40). MS (Turbo Spray): m/z=467.2 [M+H].

Workup

customwas evaporated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-7d74ab5b78e64a209d5f212cc0db032f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088930B2

Reaction notes

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