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2,5-Dibromopyridine → N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide

HRID 49572
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HRID 49572 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH:9]([NH:11][CH2:12][C:13]#[CH:14])=[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>[CH:9]([NH:11][CH2:12][C:13]#[C:14][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][CH2:12][NH:11][CH:9]=[O:10])=[N:3][CH:4]=1)=[O:10]
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참가 물질

6

반응물 2

HCID 693532,5-DibromopyridineHCID 9855445N-(prop-2-yn-1-yl)formamide

생성물 1

HCID 11413798N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide수율 93.7%

시약·촉매·용매 3

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

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온도
70 °C

실험 절차

A mixture of 2,5-dibromopyridine (100 g), N-formylpropargylamine (87.7 g), PdCl2(PPh3)2 (2.96 g), and CuI (0.2 g) in diisopropylamine (3 L) was heated at 70° C. for 6 h under a nitrogen atmosphere. The mixture was cooled to 20-22° C. and filtered. The cake was dried and then slurried in water (3 L) at 0-5° C. for 3 h. The slurry was filtered, and the cake was dried to afford 95.4 g of the title compound 9-1.

후처리

  1. temperatureThe mixture was cooled to 20-22° C.
  2. filtrationfiltered
  3. customThe cake was dried
  4. filtrationThe slurry was filtered
  5. customthe cake was dried

출처 및 근거

ORD 기록
ord-b6477a3ab4f04f7c91bc20db956d3175
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06706885B2

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