N-bromobutanimide → HCID 66850206, compound

HRID 873683Notes

Reaction equation

HRID 873683 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-8a4e3f925db64394bfd702f3e8145d2e
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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