N-bromobutanimide → 4-Bromo-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 2423169Notes

Reaction equation

HRID 2423169 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([OH:27])=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.O.C(OCC)C>[Br:8][C:22]1[C:23]([OH:27])=[CH:24][CH:25]=[C:26]2[C:21]=1[CH:20]=[CH:19][N:18]2[S:15]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:16])=[O:17]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 99705131-(Phenylsulfonyl)-1H-indol-5-ol2×

Product 1

HCID 672423064-Bromo-1-(phenylsulfonyl)-1H-indol-5-olYield 78.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

NBS (32.6 mg, 0.180 mmol) in DMF (1 mL) was added to a solution of 1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 8, 50.0 mg, 0.183 mmol) in DMF (1 mL) at room temperature. The mixture was stirred for 30 minutes and diluted with water and diethylether and transferred to a separation funnel. The organic phase was washed with water (3×), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography using 10% pentane in DCM as the eluent to give the title compound (50 mg) as a white solid. MS m/z 352/354 [M+H]+.

Workup

  1. customtransferred to a separation funnel
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2a5fc46cb1954da6b434f172a967ffbc
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

Loading…