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

HRID 873323ノート

反応式

HRID 873323 の反応式
[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

参加物

9

反応物 4

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

生成物 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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3717887112de4eb4b05f5824001c6c05
出典データセット
uspto-grants-2015_03
特許番号
US08975406B2

反応ノート

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