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

HRID 873323Notes

Reaction equation

HRID 873323 reaction equation
[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

Participants

9

Reactant 4

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

Product 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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3717887112de4eb4b05f5824001c6c05
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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