Propargyl alcohol → 4-(3-Hydroxyprop-1-yn-1-yl)-4'-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl

HRID 1519724노트

반응식

HRID 1519724 반응식
[CH2:1]([OH:4])[C:2]#[CH:3].I[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:30])[N:19]([CH:21]([C:26]([NH:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])[CH3:20])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(Cl)(Cl)Cl>[OH:4][CH2:1][C:2]#[C:3][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:30])[N:19]([CH:21]([C:26]([NH:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])[CH3:20])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

참가 물질

6

반응물 2

HCID 7859Propargyl alcoholHCID 712681754-Iodo-4'-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl

생성물 1

HCID 712681674-(3-Hydroxyprop-1-yn-1-yl)-4'-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl수율 63.7%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6212Chloroform용매

실험 절차

Prop-2-yn-1-ol (0.19 g), PdCl2(PPh3)2 (39 mg), CuI (21 mg) and TEA (0.17 g) were added to a chloroform (10 mL) solution of 4-iodo-4′-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (0.52 g) as obtained in Example 20-(1). The mixture was stirred for 3 hours at room temperature in a nitrogen atmosphere, and then the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100) to obtain 4-(3-hydroxyprop-1-yn-1-yl)-4′-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (white solid) (0.28 g, 63%).

후처리

  1. customas obtained in Example 20-(1)
  2. concentrationthe reaction mixture was concentrated
  3. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100)

출처 및 근거

ORD 기록
ord-9c61ca4563184a4f9e2eb765f32e0b4e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073821B2

반응 노트

불러오는 중…