Tributylphosphine → (4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-acetic acid methyl ester

HRID 417122

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.[CH3:28][O:29][C:30](=[O:40])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1.C(P(CCCC)CCCC)CCC.CN(C(/N=N/C(N(C)C)=O)=O)C>>[CH3:28][O:29][C:30](=[O:40])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([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:35][CH:34]=1

Participants

Reactant 4

HCID 13831Tributylphosphine

HCID 602731Methyl 2-(4-hydroxyphenoxy)acetate

HCID 5353800Diamide

HCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

Product 1

HCID 66619469(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-acetic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, int. c), (4-hydroxy-phenoxy)-acetic acid methyl ester (commercially available), tri-n-butylphosphin and N,N′,N′-tetramethylazodicarboxamide. The compound was purified by preparative HPLC (phenomenex gemini column) eluting with a gradient of acetonitril:water (50:50 to 95:5). Colorless oil. MS (Turbo Spray): m/z=555.2 [M+H].

Workup

customThe compound was purified by preparative HPLC (phenomenex gemini column)
washeluting with a gradient of acetonitril:water (50:50 to 95:5)

Sources & evidence

ORD record: ord-0daa727ca595437bb81804aa4b21e4f5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088930B2

Linked notes

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