Toluene → HCID 70855385, compound

HRID 591025Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]4[CH:19]=3)=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[O:22].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]4[C:19]=3[CH:21]([OH:22])[C:20]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(3,4-dihydro-2H-1-benzopyran-6-yl)-imidazo[1,2-a]pyridine (19b) (50 mg, 0.2 mmol), ethyl glyoxylate 50% in toluene (0.20 mL, 1.0 mmol) and p-toluenesulfonic acid (6 mg, 0.03 mmol) in ethanol (1 mL) was heated at 80° C. for 1 hour. Ethyl glyoxylate 50% in toluene (0.10 mL, 0.5 mmol) was added and the heating was maintained for one supplementary hour. The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (10 mL), washed with a saturated solution of sodium hydrogencarbonate (5 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 40/60) to provide the desired hydroxyl-ester (19c) (56 mg, 0.159 mmol, 80%) as a white solid.

Workup

temperaturethe heating was maintained for one supplementary hour
concentrationThe mixture was concentrated in vacuo
dissolutionThe residue was dissolved in ethyl acetate (10 mL)
washwashed with a saturated solution of sodium hydrogencarbonate (5 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 40/60)

Sources & evidence

ORD record: ord-929c5dfb9cfa43f9b6c678b3d42e05d1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

Loading…