Potassium Carbonate → HCID 59730380、化合物

HRID 130958ノート

反応式

HRID 130958 の反応式
[F:1][C:2]1[C:9]([F:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CC(N(C)C)=O>[F:10][C:9]1[C:2]([F:1])=[C:3]([CH:4]=[O:5])[CH:6]=[CH:7][C:8]=1[O:11][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 231070632,3-Difluoro-4-hydroxybenzaldehyde

生成物 1

HCID 59730380HCID 59730380、化合物収率 65.2%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
180 °C

実験手順

Combine 2,3-difluoro-4-hydroxy-benzaldehyde (see Canadian patent 1190093) (1.93 g, 12.2 mmol), 6-chloronicotinonitrile (1.69 g, 12.2 mmol), K2CO3 (2.53 g, 18.3 mmol) and DMA (30 ml) in a sealed, pressure vessel. Heat the suspension at 180° C. for five minutes in a microwave (600 Watts), cool to near ambient temperature and pour into aqueous NH4Cl. Extract aqueous with EtOAc (2×), wash with water (2×) and brine, dry (MgSO4) and concentrate. Purify on silica gel (20% EtOAc/Hexane) to give 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinonitrile (2.07 g) as a white solid. 1HNMR (CDCl3): 10.33 (s, 1H), 8.42 (s, 1H), 8.02 (d, 1H), 7.73 (t, 1H), 7.20 (d, 1H), 7.15 (t, 1H).

後処理

  1. temperaturecool to near ambient temperature
  2. washExtract aqueous with EtOAc (2×), wash with water (2×) and brine
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate
  5. customPurify on silica gel (20% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-3180cc77026b4d529986ccf7a170bad9
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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