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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
ノート
印刷プレビュー

反応式

HRID 2075658 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc6118eb68ae4517bf0df4a7c3e4deac
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07919621B2

反応ノート

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