Water → 6-Bromo-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 244683Notes

Reaction equation

HRID 244683 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][N:8]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 247280636-Bromo-1H-indazol-4-amine

Product 1

HCID 582558116-Bromo-1-(phenylsulfonyl)-1H-indazol-4-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-1H-indazol-4-amine (5 g) was dissolved in DMF (20 ml) and cooled in an ice bath. 60% Sodium hydride in mineral oil (0.94 g) was added portionwise and the reaction was left under an ice bath for 30 min. Benzenesulfonyl chloride (3 ml) in DMF (5 ml) was added slowly over 15 minutes and the reaction was left to warm up to room temperature overnight. Water (100 ml) was added and the reaction stirred for 20 minutes. Ethyl acetate (120 ml) was added and the water was separated, washed with ethyl acetate (50 ml×2) and the combined organics were washed with 7.5% lithium chloride (aq) (50 ml×2) then water (50 ml) before being separated and passed through a hydrophobic frit. The ethyl acetate was evaporated and the residue passed through a silica cartridge, eluting with DCM (ca. 300 ml) followed by diethyl ether (ca. 400 ml). Product containing pure fractions were combined and evaporated to dryness to give title compound, 5.9 g.

Workup

  1. temperaturecooled in an ice bath
  2. waitthe reaction was left
  3. customthe water was separated
  4. washwashed with ethyl acetate (50 ml×2)
  5. washthe combined organics were washed with 7.5% lithium chloride (aq) (50 ml×2)
  6. customwater (50 ml) before being separated
  7. customThe ethyl acetate was evaporated
  8. washeluting with DCM (ca. 300 ml)
  9. additionProduct containing pure fractions
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-22dae4a3678446918cd6111b64164fbf
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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