Methanol → Ethyl 3-chloro-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

HRID 1875034Notes

Reaction equation

HRID 1875034 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]([O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)=[O:15])([CH3:12])[CH3:11].CO>ClCCl>[Cl:1][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:14]([O:13][C:10]([CH3:9])([CH3:11])[CH3:12])=[O:15])[CH:18]=2)[NH:22][C:21]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 31398ChlorosuccinimideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 68485443Ethyl 3-chloro-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (0.044 g, 0.329 mmol) to a suspension of ethyl 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.100 g, 0.329 mmol) in dichloromethane (5 mL). Methanol (2 mL) was added to complete solution. The mixture was stirred at room temperature overnight. The solvent was evaporated, the residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (0.082 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.93 (s, 1H), 9.31 (br. s., 1H), 7.80 (br. s., 1H), 7.28-7.32 (m, 2H), 4.31 (q, 2H), 1.44 (s, 9H), 1.25-1.35 (m, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-115c467d09af4deb92eaa54f19f3c240
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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