Chloroethane → 1-Ethyl-4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

HRID 218483

反応式

HRID 218483 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]2[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]2[C:20]#[N:21])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[H-].[Na+].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:30](Cl)[CH3:31]>CN(C=O)C>[CH2:30]([N:13]1[C:14]([CH3:18])=[C:15]([C:16]#[N:17])[CH:10]([C:5]2[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[CH:4]=2)[C:11]([C:20]#[N:21])=[C:12]1[CH3:19])[CH3:31]

参加物

6

反応物 4

HCID 6337ChloroethaneHCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 597632464-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

生成物 1

HCID 690425561-Ethyl-4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (1 eq), from Synthetic Example 1, in DMF was added either NaH or Cs2CO3 (1.2 eq) at 0° C. After 30 min, ethyl chloride was introduced. The reaction mixture was stirred at rt overnight, and quenched with brine. The reaction mixture was extracted with EtOAc, washed with brine, and dried. Concentration followed by flash chromatography gave 1-ethyl-4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile. 1H-NMR (400 MHz, DMSO-D6): δ=7.86 (dd, 1H), 7.69 (m, 1H), 7.55 (t, 1H), 4.57 (s, 1H), 3.12 (q, 2H), 2.1 (s, 6H), 1.4 (t, 3H) ppm.

後処理

  1. customquenched with brine
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationConcentration

出典と根拠

ORDレコード
ord-69f6b9f24fd540fa94884e5aada17ec3
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

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