Water → HCID 178422062, compound

HRID 1631491Notes

Reaction equation

HRID 1631491 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][N:5]=2.ClC1C=C(C=CC=1)C(OO)=[O:16].O.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH3:1][C:2]1[NH:3][C:4]2=[N+:5]([O-:16])[CH:6]=[CH:7][CH:8]=[C:9]2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 5830662-Methyl-7-azaindole

Product 1

HCID 178422062HCID 178422062, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-methyl-7-azaindole (5 g, 37.8 mmol) in 1,2-dimethoxyethane (40 ml) is added m-chloroperoxybenzoic acid (10.4 g, of a 77% w/w solid, 46.6 mmol). The reaction mixture is stirred at 0° C. for 30 minutes, at room temperature for 3 hours and then poured into water (400 ml). The solution is basified to pH 9-10 using saturated potassium carbonate solution. The aqueous is extracted with DCM (2×100 ml) and the organic portions are combined, dried (MgSO4) and concentrated in vacuo. Purification of the resulting crude by chromatography on silica eluting firstly with neat ethyl acetate followed by DCM/MeOH (10:1) yields the titled compound as a yellow powder. (MH+ 297 appears as a dimer)

Workup

  1. extractionThe aqueous is extracted with DCM (2×100 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification of the resulting crude by chromatography on silica eluting firstly with neat ethyl acetate

Sources & evidence

ORD record
ord-b63129d9fcc849aba6d64b08e40b2a1c
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

Loading…