Dichloromethane → 2-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

HRID 1914935ノート

反応式

HRID 1914935 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH2:16])=O)[CH:3]=1.ClCCl.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>>[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]#[N:16])[CH:3]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 673629212-(4-Chloro-[1,8]naphthyridin-2-yl)-benzamide

生成物 1

HCID 673645562-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

実験手順

To a slurry of 970 mg (3.42 mmol) 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzamide in 10 ml dichloromethane 2.85 g (12.0 mmol) 1.26 g (5.27 mmol) methoxycarbonylsulfamoyl-triethylammonium hydroxide, inner salt, (Burgess reagent) was added. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The residue was crystallized from isopropanol yielding 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzonitrile as colourless crystals; HPLC-MS: 1.94 min, [M+H] 266.

後処理

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was crystallized from isopropanol

出典と根拠

ORDレコード
ord-66d02cab24974736bdd03333f00131f8
出典データセット
uspto-grants-2013_12
特許番号
US08614226B2

反応ノート

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