Dimethyl Sulfide → HCID 57985900, compound

HRID 1869199Notes

Reaction equation

HRID 1869199 reaction equation
[CH3:1][NH:2][C:3](=O)[CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[NH:8][CH:7]=1.S(C)C>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 57985918HCID 57985918, compound

Product 1

HCID 57985900HCID 57985900, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a RT solution of N-methyl-3-phenyl-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)-propionamide (25.3 mg, 0.091 mmol) in THF (5 mL) was added BH3.SMe2 (10 M in THF, 18 μL). The resulting mixture was refluxed for 2 h, cooled to RT, and quenched by addition of MeOH and HCl (concentrated, 3 drops). The mixture was then heated at reflux for 15 min, cooled to RT, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH), affording N-Methyl-[3-phenyl-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)-propyl]-amine. MS M+H=266.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customquenched by addition of MeOH and HCl (concentrated, 3 drops)
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 15 min
  5. temperaturecooled to RT
  6. concentrationconcentrated
  7. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-fd913ae08caa463ca4b62d802d106afa
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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