Potassium tert-butoxide → 4-[6-(1,2,3,9b-Tetraaza-cyclopenta[a]naphthalen-7-ylsulfanyl)-pyridin-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 2075716Notes

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]=[N: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][N: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

9e (110 mg, 0.28 mmol) and 4-(6-fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrile (9f, 60 mg, 0.28 mmol) were dissolved in DMF and degassed with N2 for 10 minutes. Potassium tert-butoxide (38 mg, 0.34 mmol) was added, and the reaction was degassed with N2 for another 10 minutes, and then heated to 90° C. for 2 hours. After cooling to room temperature, the mixture was concentrated and purified by silica gel chromatography to obtain the desired product, 9g.

Workup

customdegassed with N2 for 10 minutes
customthe reaction was degassed with N2 for another 10 minutes
temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-68523de087ed41cea26c9f29a091a996
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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