Potassium tert-butoxide → 4-[6-(1-Pyridin-2-yl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-pyridin-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 2075694Notes

Reaction equation

C(C(CCCC)COC(=O)C[CH2:8][S:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]1[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:21][N:22]=[C:15]1[CH:14]=[CH:13]2)C.FC1[N:40]=[C:39]([C:41]2([C:47]#[N:48])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH:38]=[CH:37][CH:36]=1.CC(C)([O-])C.[K+]>CN(C=O)C.CCOC(C)=O.O>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:20]1[N:16]2[C:17]3[C:12]([CH:13]=[CH:14][C:15]2=[N:22][N:21]=1)=[CH:11][C:10]([S:9][C:8]1[N:40]=[C:39]([C:41]2([C:47]#[N:48])[CH2:42][CH2:43][O:44][CH2:45][CH2:46]2)[CH:38]=[CH:37][CH:36]=1)=[CH:19][CH:18]=3

Participants

Conditions

Temperature: 80 °C

Procedure

5m (93 mg, 0.2 mmol) and 4-(6-Fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrile (5n, 41 mg, 0.2 mmol) were dissolved in DMF (2 mL) and degassed with N2. Potassium tert-butoxide (22 mg, 0.2 mmol) was added, and the reaction was sealed and heated to 80° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc and water, and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to obtain the desired product, 5p.

Workup

customdegassed with N2
customthe reaction was sealed
temperatureAfter cooling to room temperature
extractionthe aqueous phase was extracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-53d777e4add44f36afb18b1e3589beac
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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