Cyclohexanone → HCID 45790247, compound

HRID 2109983Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:4]1.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CO>[C:12]1([C:5]2[C:6]3[C:11](=[N:10][CH:9]=[CH:8][CH:7]=3)[NH:3][CH:4]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methanol (150 mL) was added dropwise to a chilled (0° C.) 1 L flask containing sodium hydride (60% dispersion in mineral oil, 19.3 g, 480 mmol). To the stirred suspension was added 7-azaindole (10.2 g, 86 mmol) in MeOH (100 mL) and cyclohexanone (35 mL, 340 mmol) in MeOH (65 mL). The cloudy solution was refluxed for 24 h, then the solvent was removed under reduced pressure. The oily residue was cooled in an ice bath and 3 N HCl was added with vigorous stirring until the pH=8 (pH paper). The resulting yellow ppt. was collected by filtration, washed with H2O, triturated with tBME/C6H14 (1:1, 50 mL), and dried by toluene azeotrope to give the title compound as a white solid (13.0 g, 76% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.66-1.78 (m, 2H) 1.78-1.91 (m, 2H) 2.20-2.35 (m, 2H) 2.47 (d, J=1.76 Hz, 2H) 6.28 (d, J=3.78 Hz, 1H) 7.10 (dd, J=8.06, 4.78 Hz, 1H) 7.34 (s, 1H) 8.25 (dd, J=8.06, 1.26 Hz, 1H) 8.33 (dd, J=4.66, 1.39 Hz, 1H) 11.8 (br s, 1H); 13C NMR (100 MHz, CDCl3) δ ppm 22.43, 22.98, 25.65, 27.88, 115.52, 117.31, 118.32, 121.57, 122.16, 129.39, 131.07, 141.99, 149.53.

Workup

temperatureThe cloudy solution was refluxed for 24 h
customthe solvent was removed under reduced pressure
temperatureThe oily residue was cooled in an ice bath
addition3 N HCl was added
filtrationwas collected by filtration
washwashed with H2O
customtriturated with tBME/C6H14 (1:1, 50 mL)
dry with materialdried by toluene azeotrope

Sources & evidence

ORD record: ord-b93cc0e5ae864b968c73d3f1a7cb34d7
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517872B2

Reaction notes

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