tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate

HRID 513125ノート

反応式

HRID 513125 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([C:8]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[O:9])[CH:7]=1.[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][C:27]#[CH:28])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][C:27]#[C:28][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:8](=[O:9])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[F:17])([CH3:22])([CH3:21])[CH3:20]

参加物

4

反応物 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 46835488(5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone

生成物 1

HCID 52911151tert-Butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) (5.5 g, 14.5 mmol), prop-2-ynyl-carbamic acid tert-butyl ester (2.5 g, 16 mmol), PdCl2 (PPh3)2 (0.6 g, 0.9 mmol) and Cu(I)I (0.2 g, 0.9 mmol) were suspended in anhydrous CH2Cl2 (50 mL) and the mixture was sparged with nitrogen for 30 min. Diethylamine (8 mL) was added and the solution was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes) to afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H).

後処理

  1. customthe mixture was sparged with nitrogen for 30 min
  2. additionDiethylamine (8 mL) was added
  3. concentrationThe solution was concentrated in vacuo
  4. customthe resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes)
  5. customto afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H)

出典と根拠

ORDレコード
ord-79b7c6c170304aa690d53614a72d3fbb
出典データセット
uspto-grants-2015_08
特許番号
US09102678B2

反応ノート

読み込み中…