Water → HCID 66671708, compound

HRID 634422Notes

Reaction equation

HRID 634422 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(#N)C.O>CCO.C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 95884-Fluorobenzenesulfonyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 66671708HCID 66671708, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 5-bromopyridin-3-amine (3 g, 17.34 mmol) in absolute EtOH (15 ml), 4-fluorobenzene-1-sulfonyl chloride (0.989 g, 5.08 mmol) was added and the reaction was stirred overnight. Ethanol was removed under reduced pressure and residue was diluted with DCM (40 ml) and washed once with sat. NaHCO3. Organic phase was dried over Na2SO4, filtered and concentrated. Product was straightforward purified via reverse phase chromatography with a Biotage C18 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (158 mg, 24.4% yield) as yellow pale solid.

Workup

  1. customEthanol was removed under reduced pressure and residue
  2. additionwas diluted with DCM (40 ml)
  3. washwashed once with sat. NaHCO3
  4. dry with materialOrganic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customProduct was straightforward purified via reverse phase chromatography with a Biotage C18 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Sources & evidence

ORD record
ord-024c80a27a2444b7aa85d117d06afcb6
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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