Water → HCID 54258946、化合物

HRID 365814

反応式

HRID 365814 の反応式
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])[CH:5]=[N:6][CH:7]=1.[C:16]1([CH2:22][CH2:23][CH2:24][C:25]#[CH:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCN(CC)CC.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>[C:16]1([CH2:22][CH2:23][CH2:24][C:25]#[C:26][C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[CH3:15])[CH:5]=[N:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

9

反応物 4

HCID 962WaterHCID 745735-Phenyl-1-pentyneHCID 516892Sodium BicarbonateHCID 11288721HCID 11288721、化合物

生成物 1

HCID 54258946HCID 54258946、化合物収率 81.9%

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 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (408 mg, 1.50 mmol), bis(triphenylphosphine)palladium(II) chloride (21 mg, 0.029 mmol) and copper (I) iodide (5 mg, 0.029 mmol) in CH2Cl2 (3.0 mL) and NEt3 (1.0 mL) was added 5-phenyl-1-pentyne (324 mg, 2.25 mmol). The mixture was refluxed overnight then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (411 mg, 80%). MS (CI/NH3) m/z 335 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.65-2.10 (m, 6H), 2.26-2.37 (m, 1H), 2.41-2.47 (m, 2H), 2.48 (s, 3H), 2.61-2.73 (m, 1H), 2.76-2.83 (m, 2H), 3.07-3.16 (m, 1H), 3.89-4.03 (m, 2H), 7.17-7.36 (m, 6H), 8.21-8.26 (m, 2H).

後処理

  1. temperatureThe mixture was refluxed overnight
  2. extractionThe mixture was extracted with EtOAc, which
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

出典と根拠

ORDレコード
ord-4a2de69c00024767af48f4f633003dea
出典データセット
uspto-grants-2000_10
特許番号
US06127386

関連ノート

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