2,5-Dibromopyridine → Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate

HRID 49569

반응식

HRID 49569 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[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.C(OCC)(=O)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>[Br:8][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

참가 물질

7

반응물 2

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

생성물 1

HCID 21299382Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate수율 73.8%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 7912Diisopropylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2,5-dibromopyridine (1.19 g), N-Cbz-propargylamine (1.04 g), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at ambient temperature for 3 hours under nitrogen. The mixture was diluted with ethyl acetate (50 mL). The mixture was filtered and washed with ethyl acetate (20 mL). The filtrate and wash were combined, concentrated under reduced pressure and triturated in MTBE to give crystalline 7-1 (1.28 g). The mother liquor was further purified by silica gel column chromatography using a mixture of MTBE: hexanes (1:1) to give an additional 280 mg of 7-1.

후처리

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate (20 mL)
  3. washThe filtrate and wash
  4. concentrationconcentrated under reduced pressure
  5. customtriturated in MTBE

출처 및 근거

ORD 기록
ord-26c2d7fafdc044be956e21bc0a6f0e9f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706885B2

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