Tetrahydrofuran → HCID 86723967, compound

HRID 1475349Notes

Reaction equation

HRID 1475349 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH3:13])([CH3:12])[C:9](=O)[NH:10][C:4]=2[CH:3]=1.C1COCC1>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH3:13])([CH3:12])[CH2:9][NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 867239656-Chloro-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

Product 1

HCID 86723967HCID 86723967, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

6-Chloro-3,3-dimethyl-1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one (1.4 g, 7.14 mmol) was dissolved in a solution of borane-dimethyl sulfide complex in THF (2 M, 36 mL, 71.4 mmol) and heated to 65° C. for 3 h, then cooled to ambient temperature. MeOH was added and the reaction heated at reflux for 1.5 h. After stirring overnight, the solvent was removed in vacuo. Column chromatography on silica gel (gradient elution, 0-100% EtOAc/petrol), gave the title compound (1.23 g, 95%) as a colourless solid. 1H NMR (Me-d3-OD): 7.65 (1H, s), 6.42 (1H, s), 3.43 (2H, s), 1.34 (6H, s).

Workup

  1. temperaturecooled to ambient temperature
  2. temperaturethe reaction heated
  3. temperatureat reflux for 1.5 h
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-88a521912346459c926587edaee08708
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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