Triethylamine → benzyl 5-(1H-imidazol-5-yl)pent-4-ynoate

HRID 870582ノート

反応式

HRID 870582 の反応式
I[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:8][CH2:9][C:10]#[CH:11].C(N(CC)CC)C>CN(C)C=O.O.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>[NH:3]1[C:2]([C:11]#[C:10][CH2:9][CH2:8][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:6][N:5]=[CH:4]1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 561097Benzyl pent-4-ynoateHCID 178506559HCID 178506559、化合物

生成物 1

HCID 86726543benzyl 5-(1H-imidazol-5-yl)pent-4-ynoate収率 69%

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 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Add bis(triphenylphosphine)palladium(II) chloride (0.14 g; 0.1 equiv; 0.20 mmoles) and copper(I) iodide (0.039 mg; 0.1 equiv; 0.20 mmoles) to a deoxygenated solution of 4-iodo-1H-imidazole (0.388 g; 1.0 equiv; 2.00 mmoles), benzyl pent-4-ynoate (0.376 g; 1.0 equiv; 2.00 mmoles), and triethylamine (0.84 mL; 3 equiv; 6.0 mmoles) in dimethylformamide (8 mL). Heat the mixture to 75° C. for 16 hours, then dilute the mixture with water (30 mL) and extract 3× with ethyl acetate. Wash the combined organic extracts with brine, dry over magnesium sulfate, filter, and concentrate to provide the crude product. Purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford benzyl 5-(1H-imidazol-5-yl)pent-4-ynoate (0.35 g; 69%) as a colorless oil: MS (m/z): 255(M+1).

後処理

  1. extractionextract 3× with ethyl acetate
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto provide the crude product
  7. customPurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-155eecd8ed134ae3b01bebfc5ff72213
出典データセット
uspto-grants-2015_03
特許番号
US08969555B2

反応ノート

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