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

HRID 49569ノート

反応式

HRID 49569 の反応式
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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

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HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26c2d7fafdc044be956e21bc0a6f0e9f
出典データセット
uspto-grants-2004_03
特許番号
US06706885B2

反応ノート

読み込み中…