Benzene, 1-fluoro-4-(trifluoromethyl)- → [5-Methanesulfonyl-2-((r)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[3-(4-trifluoromethyl-phenoxy)-azetidin-1-yl]-methanone

HRID 1711763Notes

Reaction equation

HRID 1711763 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=2[O:18][C@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[O:7])[CH2:3]1.F[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1>>[CH3:17][S:14]([C:12]1[CH:11]=[CH:10][C:9]([O:18][C@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[C:8]([C:6]([N:4]2[CH2:3][CH:2]([O:1][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[CH2:5]2)=[O:7])[CH:13]=1)(=[O:15])=[O:16]

Participants

3

Reactant 2

HCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 58673082(3-Hydroxy-azetidin-1-yl)-[5-methanesulfonyl-2-((R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Product 1

HCID 11562544[5-Methanesulfonyl-2-((r)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[3-(4-trifluoromethyl-phenoxy)-azetidin-1-yl]-methanoneYield 9%

Procedure

Prepared in analogy to Example 21(b) from (3-hydroxy-azetidin-1-yl)-[5-methanesulfonyl-2-((R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone and 4-fluorobenzotrifluoride. The crude material was purified by flash chromatography (methanol/dichloromethane) to yield the title compound as a white crystalline solid (yield 9%). MS (m/e): 512.3 (M+H+, 100%).

Workup

  1. customThe crude material was purified by flash chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-43dbf78e03054ec5a7353514e10e4c9b
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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