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Methanesulfonamide → [2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

HRID 8126
Notes
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Reaction equation

HRID 8126 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C[Al](C)C.[C:10]([O:14][C:15](=[O:36])[NH:16][C:17]([CH3:35])([CH3:34])[CH2:18][C:19]1[C:27]2[C:22](=[C:23]([C:28]([O:30][CH2:31]OC)=[O:29])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)([CH3:13])([CH3:12])[CH3:11]>ClCCl>[C:10]([O:14][C:15](=[O:36])[NH:16][C:17]([CH3:35])([CH3:34])[CH2:18][C:19]1[C:27]2[C:22](=[C:23]([C:28]([O:30][CH2:31][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:29])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)([CH3:12])([CH3:13])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 16682925TrimethylaluminumHCID 69517575[2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69518509[2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl esterYield 117.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution of methanesulfonamide (106 mg, 1.12 mmol) and trimethyl aluminum (2.0 M in hexanes, 0.56 ml, 1.12 mmol) in dry dichloromethane (5.0 ml) is stirred at room temperature under a nitrogen atmosphere for 20 minutes. A solution of [2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (160 mg, 0.425 mmol) in dry dichloromethane (1.5 ml) is added and the mixture is heated under reflux for 15 hours. The mixture is cooled to room temperature and quenched with 1 N HCl solution (3.4 ml) and partitioned between ethyl acetate and water. The organic extracts are dried over anhydrous Na2SO4, filtered and the solvent evaporated to give 220 mg of [2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (90%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. customquenched with 1 N HCl solution (3.4 ml)
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic extracts are dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-d6abe5dd3fb941639e55b4abc3d4079d
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes