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

HRID 49571

반응식

HRID 49571 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 7912Diisopropylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23e7eb85123f438d84ad90e4f736190c
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706885B2

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