Potassium tert-butoxide → HCID 178419838, compound

HRID 1854497Notes

Reaction equation

HRID 1854497 reaction equation
Cl[C:2]1[C:3]([C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:12][OH:13])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH:14]1([C:11]2[C:3]3=[C:4]4[CH:10]=[CH:9][NH:8][C:5]4=[N:6][CH:7]=[C:2]3[O:13][N:12]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 136342280HCID 136342280, compound

Product 1

HCID 178419838HCID 178419838, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanone oxime (0.19 g, 0.70 mmol) and potassium tert-butoxide (0.16 g, 1.4 mmol) in DMSO (6 mL) was heated in a Biotage microwave at about 125° C. for about 30 min. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography (0-30% EtOAc in heptane gradient as the eluent to afford 1-cyclohexyl-6H-isoxazolo[4,5-d]pyrrolo[2,3-b]pyridine as a white solid (0.076 g, 46%): LC/MS (Table 2, Method d) Rt=2.50 min; m/z: 242 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by silica gel chromatography (0-30% EtOAc in heptane gradient as the eluent

Sources & evidence

ORD record
ord-1347b9413f544faca0e4442b08297f3f
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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