Ethyl Acetate → Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate

HRID 49571

反応式

HRID 49571 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([NH:16][CH2:17][C:18]#[CH:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[C:20]([NH:30][CH2:31][C:32]#[CH:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(OCC)(=O)C>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>[C:12]([O:11][C:9]([NH:16][CH2:17][C:18]#[C:19][C:2]1[N:3]=[CH:4][C:5]([C:33]#[C:32][CH2:31][NH:30][C:20](=[O:21])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][CH:7]=1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 693532,5-DibromopyridineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 11137906Benzyl prop-2-yn-1-ylcarbamate

生成物 1

HCID 21299383Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate収率 11.9%

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

実験手順

A mixture of 2,5-dibromopyridine (1.19 g), N-Boc-propargylamine (781 mg), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at room temperature overnight under nitrogen atmosphere. To the mixture was added N-Cbz-propargylamine (1.14 g) and the mixture was heated under reflux temperature for 5 hours under nitrogen atmosphere. The mixture was cooled to room temperature. To the mixture was added ethyl acetate (50 mL). The precipitates were filtered and washed with ethyl acetate. The filtrate and washings were combined and purified by silica gel column to give 6-1 (250 mg) as a crystalline compound.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux temperature for 5 hours under nitrogen atmosphere
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe precipitates were filtered
  5. washwashed with ethyl acetate
  6. custompurified by silica gel column

出典と根拠

ORDレコード
ord-23e7eb85123f438d84ad90e4f736190c
出典データセット
uspto-grants-2004_03
特許番号
US06706885B2

関連ノート

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