Diisobutylaluminumhydride → N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

HRID 2170307

반응식

HRID 2170307 반응식
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11](N(OC)C)=[O:12])[C:8]([Br:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Br:17][C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:10][C:9]=1[CH:11]=[O:12]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 902804776-acetamido-3-bromo-N-methoxy-N-methylpicolinamide

생성물 1

HCID 90280237N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the crude material from last step (1B, 2.6 g, 8.6 mmol) in THF (tetrahydrofuran)(30 mL) was added DIBAL-H (diisobutylaluminium hydride)(13 mmol, 1.5 equiv) dropwise at 70° C. The reaction was stirred for 1 h and was then quenched with NH4Cl solution. The reaction mixture was partitioned between EtOAc and saturated NH4Cl solution. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was used in the next step without further purification. MS (m/z) 244.1 [M+H]+.

후처리

  1. customwas then quenched with NH4Cl solution
  2. customThe reaction mixture was partitioned between EtOAc and saturated NH4Cl solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was used in the next step without further purification

출처 및 근거

ORD 기록
ord-2eb5869b1a384c52a45f79d471c447f1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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