5-Bromopyrimidine → 5-[2-(2-Chloro-4-pyrimidin-5-yl-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

HRID 2386875Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[CH:17]([CH3:35])[C:18]([C:24]1[CH:25]=[CH:26][C:27]2[O:31][C:30](=[O:32])[N:29]([CH3:33])[C:28]=2[CH:34]=1)([OH:23])[C:19]([F:22])([F:21])[F:20].Br[C:37]1[CH:38]=[N:39][CH:40]=[N:41][CH:42]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:37]2[CH:38]=[N:39][CH:40]=[N:41][CH:42]=2)[CH:5]=[CH:4][C:3]=1[CH:17]([CH3:35])[C:18]([C:24]1[CH:25]=[CH:26][C:27]2[O:31][C:30](=[O:32])[N:29]([CH3:33])[C:28]=2[CH:34]=1)([OH:23])[C:19]([F:20])([F:22])[F:21]

Participants

Reactant 2

HCID 783445-Bromopyrimidine

HCID 66697095HCID 66697095, compound

Product 1

HCID 666969785-[2-(2-Chloro-4-pyrimidin-5-yl-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

Procedure

The title compound was prepared in analogy to Example 186, step 2 from 5-{2-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-3-methyl-3H-benzooxazol-2-one (obtained in Example 186, step 1) with 5-bromopyrimidine [CAS Reg. No. 4595-59-9]. MS (m/e)=464.1 [M+H+].

Sources & evidence

ORD record: ord-804d41bd92454ea3968d2bcfa8fb53ec
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Reaction notes

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