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4-(6-Fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrile → 4-[6-(Imidazo[1,2-a]quinolin-7-ylsulfanyl)-pyridin-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 2075658
Notes
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Reaction equation

HRID 2075658 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[CH: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>CN(C=O)C>[CH: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 582577824-(6-Fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrileHCID 670909063-(Imidazo[1,2-a]quinolin-7-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester

Product 1

HCID 670912914-[6-(Imidazo[1,2-a]quinolin-7-ylsulfanyl)-pyridin-2-yl]-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1i (261 mg, 0.6 mmol) and 4-(6-Fluoro-pyridin-2-yl)-tetrahydro-pyran-4-carbonitrile (1j, 123 mg, 0.6 mmol) were dissolved in DMF and degassed with N2 for 10 minutes. Potassium tert-butoxide (81 mg, 0.72 μmmol) was added, and the mixture was degassed with N2 for an additional 10 minutes. The reaction was heated to 90° C. for 24 hours, then cooled to room temperature. The solution was diluted with EtOAc and water, and the aqueous layer 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, 1k.

Workup

  1. customdegassed with N2 for 10 minutes
  2. additionPotassium tert-butoxide (81 mg, 0.72 μmmol) was added
  3. customthe mixture was degassed with N2 for an additional 10 minutes
  4. temperaturecooled to room temperature
  5. additionThe solution was diluted with EtOAc and water
  6. extractionthe aqueous layer was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bc6118eb68ae4517bf0df4a7c3e4deac
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919621B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes