Triethylamine → Tert-butyl (4-chloro-3-(cyclohexylethynyl)pyridin-2-yl)carbamate

HRID 1521956ノート

反応式

HRID 1521956 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1I.[C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[CH:18].C(N(CC)CC)C>O1CCCC1.[Cu]I.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>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:18]#[C:17][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 598528862-Boc-Amino-3-iodo-4-chloropyridine

生成物 1

HCID 131733115Tert-butyl (4-chloro-3-(cyclohexylethynyl)pyridin-2-yl)carbamate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

tert-Butyl 4-chloro-3-iodopyridin-2-ylcarbamate (1.0 g, 2.82 mmol) in 10 mL tetrahydrofuran was treated with copper(I) iodide (0.027 g, 0.141 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.099 g, 0.141 mmol) and the mixture was purged with nitrogen for 5 minutes. Ethynylcyclohexane (0.472 mL, 3.67 mmol) and triethylamine (1.179 mL, 8.46 mmol) were added and the mixture was stirred overnight under nitrogen. The mixture was filtered through diatomaceous earth and the filtrate washed with aqueous citric acid (once), water (twice), and brine (once), dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) provided the title compound. MS (DCI) m/e 335/337 (M+H)+.

後処理

  1. customthe mixture was purged with nitrogen for 5 minutes
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe filtrate washed with aqueous citric acid (once), water (twice), and brine (once),
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-c6ff736f33a24db7a4ef7cba4d64c824
出典データセット
uspto-grants-2015_07
特許番号
US09073922B2

反応ノート

読み込み中…