Water → HCID 86715099, compound

HRID 533908Notes

Reaction equation

HRID 533908 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([O:8][C@@H:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])=[CH:4][CH:3]=1.[CH3:15][S-:16].[Na+].CN(C=O)C.O>CC(=O)OCC>[CH3:15][S:16][C:2]1[N:7]=[CH:6][C:5]([O:8][C@@H:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 86715100HCID 86715100, compound

Product 1

HCID 86715099HCID 86715099, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-3-(6-bromo-pyridin-3-yloxy)-pyrrolidin-2-one (0.8 g), sodium methanethiolate (327 mg) and DMF (15 mL) was heated to 100° C. for 15 minutes. After the mixture reached room temperature, it was distributed between water and EA. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by preparative HPLC to provide the title compound. MS ESI+: m/z=225 [M+H]+.

Workup

  1. customreached room temperature
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3a26957d90174e8c9cfbe03157da65eb
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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