Ethylparaben → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-benzoic acid ethyl ester

HRID 417063Notes

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.O[C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:36]([O:35][C:33](=[O:34])[C:32]1[CH:38]=[CH:39][C:29]([O:15][CH2:14][CH:13]([N:12]2[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:30][CH:31]=1)[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 0.3 g (0.77 mmol) 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, int. c) in 3 mL tetrahydrofuran, 0.13 g (0.84 mmol) ethyl 4-hydroxybenzoate and 0.22 g (084 mmol) triphenylphosphine were added. The solution was cooled to 0° C., 0.15 g (0.84 mmol) diethyl azodicarboxylate dissolved in 2 mL tetrahydrofuran were added dropwise and the reaction stirred at room temperature for 18 h. The reaction was adsorbed on silica gel and purified by silica gel column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 100:40 v/v) to yield the title compound as a white foam (55%). MS (Turbo Spray): m/z=539.2 [M+H].

Workup

additionwere added dropwise
custompurified by silica gel column chromatography
washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 100:40 v/v)

Sources & evidence

ORD record: ord-f980afbfb9794b078ac2880357bba23a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088930B2

Reaction notes

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