Methylamine → 1-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide

HRID 1475323Notes

Reaction equation

HRID 1475323 reaction equation
[CH3:1][NH2:2].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:19])=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:13]=2)[C:8]([CH3:21])([CH3:20])[CH2:7]1)(=[O:5])[CH3:4]>C1COCC1>[CH3:1][NH:2][S:15]([C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:21])([CH3:20])[CH2:7][N:6]2[C:3](=[O:5])[CH3:4])=[CH:10][C:11]=1[Br:19])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 867239431-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride

Product 1

HCID 709804931-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (2 M solution in THF, 2.4 mL, 4.9 mmol) was added to a solution of 1-acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride (300 mg, 0.82 mmol) in THF (10 mL). The solution was stirred at room temperature for 30 minutes then the solvent was removed in vacuo and the residue partitioned between water and EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (271 mg) as a yellow solid. 1H NMR (CDCl3): 8.93 (1H, s), 7.44 (1H, s), 5.07 (1H, s), 3.88 (2H, s), 2.68 (3H, d), 2.25 (3H, s), 1.48-1.22 (6H, s).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c2394c4753c41aba27788f136bc4d90
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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