Sodium hydride → HCID 86723311、化合物

HRID 2366225

反応式

HRID 2366225 の反応式
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([F:24])[C:14]=1[C:15](Cl)=[O:16]>CN(C=O)C>[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([F:24])[C:14]=1[C:15]([N:9]([C:15](=[O:16])[C:14]1[C:18]([F:24])=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:13]=1[Cl:12])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:16]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 601502892-Chloro-3-fluoropyridin-4-amineHCID 866489652-Chloro-4-cyano-6-fluorobenzoyl chloride

生成物 1

HCID 86723311HCID 86723311、化合物収率 39.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 2-chloro-3-fluoropyridin-4-ylamine (1.05 g, 7.1 mmol) in DMF (25 mL) at 0° C. was added sodium hydride (0.343 g, 14.3 mmol). The resulting violet mixture stirred for 20 minutes before a solution of 2-chloro-4-cyano-6-fluoro-benzoyl chloride (1.87 g, 8.6 mmol) in DMF (10 mL) was added. The mixture was warmed to room temperature stirred for 16 hours, then quenched with water and 1M HCl. The mixture was filtered through Celite®, washing with EtOAc. The organic filtrate was dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography eluting with DCM to give the desired compound as an off-white foam (0.869 g, 25% yield). 1H NMR (300 MHz, CDCl3): δ 8.24 (d, J=5.1 Hz, 1H), 7.55 (s, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.32-7.23 (m, 1H).

後処理

  1. additionwas added
  2. customquenched with water and 1M HCl
  3. filtrationThe mixture was filtered through Celite®
  4. washwashing with EtOAc
  5. dry with materialThe organic filtrate was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel flash chromatography
  8. washeluting with DCM

出典と根拠

ORDレコード
ord-fe8da4329c3744f4a8ed96107016a7ce
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

関連ノート

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