Potassium tert-butoxide → 4-[6-([1,2,4]Triazolo[1,5-a]quinolin-7-ylsulfanyl)-pyridin-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 2075711Notes

Reaction equation

C(C(CCCC)CO[C:6](=O)[CH2:7][CH2:8][S:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]1[N:20]=[CH:21][N:22]=[C:15]1[CH:14]=[CH:13]2)C.FC1[N:34]=[C:33]([C:35]2([C:41]#[N:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=CC=1.CC(C)([O-])C.[K+]>CN(C=O)C>[N:20]1[N:16]2[C:17]3[C:12]([CH:13]=[CH:14][C:15]2=[N:22][CH:21]=1)=[CH:11][C:10]([S:9][C:8]1[N:34]=[C:33]([C:35]2([C:41]#[N:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=[CH:6][CH:7]=1)=[CH:19][CH:18]=3

Participants

Conditions

Temperature: 90 °C

Procedure

8e (201 mg, 0.50 mmol) and 4-(6-Fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrile (8f, 105 mg, 0.51 mmol) were dissolved in DMF at room temperature and degassed for 10 minutes with N2. Potassium tert-butoxide (67 mg, 0.60 mmol) was added, and the mixture was degassed with N2 for another 10 minutes. The reaction was heated to 90° C. for 12 hours, and then concentrated and purified by silica gel chromatography (25-50% EtOAc in hexanes) to give the desired product, 8g.

Workup

customdegassed for 10 minutes with N2
customthe mixture was degassed with N2 for another 10 minutes
concentrationconcentrated
custompurified by silica gel chromatography (25-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-62db0cd31e9945218522673cca86d3a5
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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