N-bromobutanimide → HCID 67315809, compound

HRID 1013305Notes

Reaction equation

HRID 1013305 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[NH:11]2.[Br:21]N1C(=O)CCC1=O>ClCCl.O1CCCC1>[Br:21][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:20])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67316099Methyl 4-o-tolyl-1h-indole-2-carboxylate

Product 1

HCID 67315809HCID 67315809, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of EXAMPLE 126A (205 mg) in dichloromethane (5 ml) and tetrahydrofuran (5 ml) at 0° C. was added dropwise N-bromosuccinimide (144 mg) in tetrahydrofuran (3 ml). The mixture was stirred while the ice bath slowly reached room temperature. The reaction mixture was concentrated and the residue was dissolved in dichloromethane and purified by flash chromatography, eluting with 0-100% dichloromethane in hexane to provide the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. custompurified by flash chromatography
  4. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-e970a1dd4af74878830c840d12a0a5f4
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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