Methanol → HCID 86724025, compound

HRID 1475453Notes

Reaction equation

HRID 1475453 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:13][CH3:14])([CH3:12])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:13][CH3:14])([CH3:12])[CH2:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 70980081HCID 70980081, compound

Product 1

HCID 86724025HCID 86724025, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

BH3-Me2S (2 M in THF, 5.7 mL, 11.5 mmol) was added to a solution of 6-chloro-3-ethyl-3-methyl-1,3-dihydro-indol-2-one (240 mg, 1.1 mmol) in THF (10 mL). The reaction mixture was stirred at 70° C. for 3 h. The reaction was cooled to room temperature and MeOH (ca. 20 mL) was carefully added. The resulting solution was heated at reflux for 2 h. The solvents were then removed in vacuo and the residue was purified by flash chromatography to give the title compound (147 mg) as a colourless oil. MS: [M+H]+=196.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 2 h
  4. customThe solvents were then removed in vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7044ac60cdac4e77b19d32f1cd1c1a74
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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