2,5-Dibromopyridine → Benzyl 3-[5-(3-{[(benzyloxy)carbonyl]amino}prop-1-ynyl)pyridin-2-yl]prop-2-ynylcarbamate

HRID 49570ノート

反応式

HRID 49570 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([NH:19][CH2:20][C:21]#[CH:22])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>C(NC(C)C)(C)C.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>[CH2:12]([O:11][C:9]([NH:19][CH2:20][C:21]#[C:22][C:5]1[CH:6]=[CH:7][C:2]([C:22]#[C:21][CH2:20][NH:19][C:9](=[O:10])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 2

HCID 693532,5-DibromopyridineHCID 11137906Benzyl prop-2-yn-1-ylcarbamate

生成物 1

HCID 11453795Benzyl 3-[5-(3-{[(benzyloxy)carbonyl]amino}prop-1-ynyl)pyridin-2-yl]prop-2-ynylcarbamate収率 86.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 7912Diisopropylamine溶媒

反応条件

温度
65 °C

実験手順

A mixture of 2,5-dibromopyridine (3.00 g), N-Cbz-propargylamine (5.99 g), PdCl2(PPh3)2 (89.8 mg), and CuI (6.0 mg) in diisopropylamine (51 ml) was heated at 65° C. for 7 hours under nitrogen atmosphere. The mixture was cooled to room temperature, and the precipitates were filtered, washed with water, and dried under reduced pressure to give 8-1 (4.96 g) as a crystalline compound; m.p. 156-158° C.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe precipitates were filtered
  3. washwashed with water
  4. customdried under reduced pressure

出典と根拠

ORDレコード
ord-f7d435b7b14c4dde8385d203e4bb50ac
出典データセット
uspto-grants-2004_03
特許番号
US06706885B2

反応ノート

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