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 513125노트

반응식

HRID 513125 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-79b7c6c170304aa690d53614a72d3fbb
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102678B2

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