Potassium tert-butoxide → HCID 49793321, compound

HRID 2369374Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[S:14][CH:13]=[N:12][C:11]=2[NH:15]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>CN1C(=O)CCC1.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:15][C:11]3[N:12]=[CH:13][S:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

238 mg (0.75 mmol) of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate are dissolved in 4.5 ml of NMP in a microwave vessel, and 143 mg (1.27 mmol) of KOtBu are added. The reaction vessel is sealed under nitrogen and heated at 90° C. for 20 min in the microwave while cooling in a stream of nitrogen. The mixture is diluted with 50 ml of diethyl ether and washed with 50 ml of sat. NaCl solution. The aqueous phase is again extracted with diethyl ether. The combined organic phases are dried over sodium sulfate, evaporated in vacuo, and the residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1), giving 109 mg (0.49 mmol, 66%) of 5-(4-fluorophenyl)-4H-pyrrolo[2,3-d]-1,3-thiazole as white crystals; m.p. 244-245;

Workup

customThe reaction vessel is sealed under nitrogen
temperaturewhile cooling in a stream of nitrogen
washwashed with 50 ml of sat. NaCl solution
extractionThe aqueous phase is again extracted with diethyl ether
dry with materialThe combined organic phases are dried over sodium sulfate
customevaporated in vacuo
customthe residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1)

Sources & evidence

ORD record: ord-c96cb0ced1e845faa7b3b8792581b363
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703961B2

Reaction notes

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