N-bromobutanimide → HCID 66850206, compound

HRID 1810211Notes

Reaction equation

HRID 1810211 reaction equation
[Si:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([Cl:36])=[C:23]([S:25]([NH:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])(=[O:27])=[O:26])[CH:24]=3)=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:37]N1C(=O)CCC1=O>O1CCCC1.C(OCC)C>[Br:37][C:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([Cl:36])=[C:23]([S:25]([NH:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])(=[O:27])=[O:26])[CH:24]=3)=[O:18])=[CH:13][CH:12]=2)[N:8]([Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66850346HCID 66850346, compound

Product 1

HCID 66850206HCID 66850206, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.7 g of 5-[1-(tert-butyldimethylsilyl)-1H-indole-6-carbonyl]-2-chloro-N-(tert-butyldimethylsilyl)-benzenesulfonamide in tetrahydrofuran (110 mL) at −78° C. is treated with 0.564 g of N-bromosuccinimide. After 6 h at −78° C. the temperature is allowed to reach room temperature. The reaction mixture is taken up in diethyl ether, washed with water and dried (magnesium sulfate). The solvent is evaporated and the residue is triturated under sonication with diisopropylether to give 5-[3-bromo-1-(tert-butyldimethylsilyl)-1H-indole-6-carbonyl]-2-chloro-N-(tert-butyldimethylsilyl)-benzenesulfonamide as a tan powder. MS (m/z): 643 (M+1); Rf 0.90 (95:5 methylene chloride/methanol).

Workup

  1. customto reach room temperature
  2. washwashed with water
  3. dry with materialdried (magnesium sulfate)
  4. customThe solvent is evaporated
  5. customthe residue is triturated under sonication with diisopropylether

Sources & evidence

ORD record
ord-4016b96b648a4b7faa7e92227ce3e88e
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

Loading…