Methanol → HCID 86745336, compound

HRID 1461646Notes

Reaction equation

HRID 1461646 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]3SC)[CH:5]=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].CO>[Ni].CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[CH:5]=[CH:4][C:3]=1[C:21]([F:24])([F:22])[F:23]

Participants

5

Reactant 2

HCID 887MethanolHCID 86745337HCID 86745337, compound

Product 1

HCID 86745336HCID 86745336, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 5-[(2-chloro-α,α,α-tri- fluoro-p-tolyl)oxy]-3-(methylthio)-2-indolinone (25.0 g, 0.067 mol) in a 5:1 mixture of methanol and dimethylformamide is heated to 50° C., under a nitrogen atmosphere, treated portionwise with an aqueous slurry of Raney nickel W-2 catalyst until disulfurization is complete as determined by chromatography, cooled to room temperature and filtered through a bed of diatomaceous earth. The filtrate is concentrated in vacuo, diluted with a 1:1 mixture of ethyl acetate and ether, washed with water, dried over MgSO4 and reconcentrated in vacuo to afford the title product as a tan solid, 16.5 g (75%), identified by 1HNMR analysis.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a bed of diatomaceous earth
  3. concentrationThe filtrate is concentrated in vacuo
  4. additiondiluted with a 1:1 mixture of ethyl acetate and ether
  5. washwashed with water
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-fc62668b46bd4bef9d34fe7c5c0d17ee
Source dataset
uspto-grants-1991_12
Patent number
US05076835

Reaction notes

Loading…