2-Chloro-6-fluorobenzyl bromide → HCID 66920546, 화합물

HRID 1510089노트

반응식

HRID 1510089 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2Cl)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Cl:37][C:38]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:39]=1[CH2:40]Br>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[CH2:40][C:39]2[C:42]([F:46])=[CH:43][CH:44]=[CH:45][C:38]=2[Cl:37])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 27736252-Chloro-6-fluorobenzyl bromideHCID 45257316HCID 45257316, 화합물HCID 178418339Butyllithium

생성물 1

HCID 66920546HCID 66920546, 화합물수율 34.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 500 mg (1.14 mmol) of the compound of example 16, step 1, in THF (8 ml) was cooled to −78° C. with an acetone/dry ice bath. Within 10 min a solution of n-butyllithium (0.55 ml, 1.36 mmol, 2.5 M in hexane) was added followed by 0.36 ml (2.27 mmol) of 2-chloro-6-fluoro-benzyl bromide. The cooling bath was removed and the reaction mixture was allowed to warm up slowly to room temperature and stirred overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 216 mg of the title compound.

후처리

  1. customThe cooling bath was removed
  2. customThe mixture was quenched with water
  3. extractionextracted with EA
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative HPLC
  9. waitThe eluate was lyophilized overnight

출처 및 근거

ORD 기록
ord-4c6d6e091ed447a481f448852530ff3f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211885B2

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