Dimethylformamide → (5-Bromo-3-fluoro-pyridin-2-yl)-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 873323노트

반응식

HRID 873323 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:11][S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].CN(C=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH2:8][N:18]2[CH2:19][CH2:20][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]([N:18]2[CH2:19][CH2:20][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[O:9])=[N:6][CH:7]=1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 7091611-(Methylsulfonyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 210758705-Bromo-3-fluoropyridine-2-carbaldehyde

생성물 2

HCID 70978953(5-Bromo-3-fluoro-pyridin-2-yl)-(4-methanesulfonyl-piperazin-1-yl)-methanoneHCID 709790061-((5-Bromo-3-fluoropyridin-2-yl)methyl)-4-(methylsulfonyl)piperazine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

5-Bromo-3-fluoropicolinaldehyde (94 mg, 0.46 mmol) and 1-(methylsulfonyl)piperazine (82 mg, 0.5 mmol) were stirred in AcOH (0.11 mL) and DMF (1 mL) at rt. NaBH(OAc)3 (160 mg, 0.75 mmol) was added slowly and the reaction mixture stirred at room temperature for 3.5 h. Water and DCM were added and the aqueous phase was extracted with DCM. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give 1-((5-bromo-3-fluoropyridin-2-yl)methyl)-4-(methylsulfonyl)piperazine (Intermediate 7) as a colourless solid.

후처리

  1. customat rt
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3717887112de4eb4b05f5824001c6c05
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975406B2

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