Benzenesulfonyl chloride → 1-benzenesulfonyl-3-bromo-6-nitro-1H-indole

HRID 2079890

Reaction equation

HRID 2079890 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][CH:10]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:21]1([S:27]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[C:9]([Br:8])=[CH:10]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 147079343-Bromo-6-nitro-1H-indole3×

Product 1

HCID 574421961-benzenesulfonyl-3-bromo-6-nitro-1H-indole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add triethyl amine (Et3N) (6.7 mL, 48 mmol, 4 eq) and DMAP (240 mg, 2.0 mmol, 0.1 eq) to a slurry of 3-bromo-6-nitro indole, 2 (4.82 g, 20 mmol) in 100 mL of CH2Cl2. Let the solution stir until the 3-bromo-6-nitro indole dissolves and then add benzenesulfonyl chloride (3.1 mL, 24 mmol, 1.2 eq). Let the solution stir overnight. Filter off the precipitate, which forms, wash the precipitate with CH2Cl2, and collect the filtrates to give 6.83 g of the title compound. Sequentially wash the combined filtrates with 1 M HCl, saturated sodium bicarbonate, and brine. Dry the organic layer over Na2SO4, filter, and then concentrate the filtrate. Boil the resulting solid in ˜30 mL of CH2Cl2 and a little MeOH, add 30 mL hexanes, let cool, and then filter off the precipitate to give another 1.3 g of the title compound. 1H NMR (DMSO-d6) δ 8.74 (d, 1H, J=2.2 Hz), 8.58 (s, 1H), 8.19 (dd, 1H, J=2.2, 8.8 Hz), 8.08-8.05 (m, 2H), 7.75-7.68 (m, 2H), 7.63-7.59 (m, 2H)—.

Workup

  1. dissolutiondissolves
  2. filtrationFilter off the precipitate, which
  3. washwash the precipitate with CH2Cl2
  4. customcollect the filtrates

Sources & evidence

ORD record
ord-dce792d4c44f465785ea57da36d9e14c
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Linked notes

Loading…