Potassium Carbonate → 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2264231Notes

Reaction equation

HRID 2264231 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([S:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][N:23]=3)[CH:18]=[CH:17]2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:25]NC(=O)CCC(N)=O>C1COCC1>[C:7]1([S:13]([N:16]2[C:24]3=[N:23][CH:22]=[CH:21][CH:20]=[C:19]3[C:18]([Br:25])=[CH:17]2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 9834204N-Bromosuccinamide

Product 1

HCID 455881343-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (47.1 g) was added to a solution of N-phenylsulfonyl-7-azaindole (1c) (80.0 g) in THF (500 mL) at 0° C. N-Bromosuccinamide (60.6 g) was then added portionwise to the suspension. The reaction mixture was warmed to rt and stirred for 2 days. It was quenched with water and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, then dried over Na2SO4 and concentrated. The residue was subjected to silica gel column (eluted with 7:3 dichloromethane/hexane) to give 1-benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-b]pyridine (1d) (50.78 g, 49%). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=4.8 Hz, 1H), 8.20 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.0 Hz, 1H), 7.78 (s, 1H), 7.62 (t, J=7.6 Hz, 1H), 7.50 (t, J=7.6 HZ, 2H), 7.26 (m, 1H).

Workup

  1. customIt was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. washThe residue was subjected to silica gel column (eluted with 7:3 dichloromethane/hexane)

Sources & evidence

ORD record
ord-949fe8753ed143e5a92f25fb471fb8e3
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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