Cesium carbonate → HCID 89444009, 화합물

HRID 1771809노트

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HRID 1771809 반응식
[F:1][C:2]1[C:3]([NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[F:26])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[C:5]#[N:6].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36]>CC(C)=O>[C:5]([C:4]1[C:3]([NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[F:26])=[C:2]([F:1])[CH:9]=[CH:8][C:7]=1[O:10][CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])#[N:6]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 121593Isopropyl bromoacetateHCID 89445280HCID 89445280, 화합물

생성물 1

HCID 89444009HCID 89444009, 화합물수율 59.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-fluoro-2-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-6-hydroxy-benzonitrile (360 mg, 1.0 mmol, 1 eq) in acetone was added Cs2CO3 (651.6 mg, 2.0 mmol, 2 eq). The reaction was stirred for 30 min at room temperature then isopropyl 2-bromoacetate (221 mg, 1.2 mmol, 1.2 eq) was added. The reaction was stirred for a further 2 h, then quenched with water and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 50:1 to 10:1) to give the title compound as a colorless oil (270 mg, 59%).

후처리

  1. stirringThe reaction was stirred for a further 2 h
  2. customquenched with water
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by column chromatography (petroleum ether:EtOAc, 50:1 to 10:1)

출처 및 근거

ORD 기록
ord-83b7d6c309f04561a823698465455647
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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