Piperidine → 1-{2-[4-(4-Bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidine

HRID 1916730ノート

反応式

HRID 1916730 の反応式
N1CCCCC1.[Br:7][C:8]1[CH:9]=[C:10]([C:13]#[CH:14])[S:11][CH:12]=1.I[C:16]1[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1>C1COCC1.[Cu]I>[Br:7][C:8]1[CH:9]=[C:10]([C:13]#[C:14][C:16]2[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:18][CH:17]=2)[S:11][CH:12]=1

参加物

6

反応物 3

HCID 8082PiperidineHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidineHCID 534266384-Bromo-2-ethynylthiophene2 回

生成物 1

HCID 673623061-{2-[4-(4-Bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere 0.3 mL (3.13 mmol) piperidine, 14.9 mg (0.08 mmol) CuI and 90.3 mg (0.08 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 293 mg (1.56 mmol) 4-bromo-2-ethynyl-thiophene and 620 mg (1.56 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine in 10 mL THF and the reaction mixture is stirred overnight at RT. To complete the reaction another 150 mg (0.8 mmol) 4-bromo-2-ethynyl-thiophene are added and the mixture is stirred for a further 24 h at RT. The mixture is evaporated down i. vac., the residue is triturated with EtOAc and the insoluble ingredients are filtered off. After the solvent has been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 8:2:0.2).

後処理

  1. additionare added
  2. stirringthe mixture is stirred for a further 24 h at RT
  3. customThe mixture is evaporated down i
  4. custom, the residue is triturated with EtOAc
  5. filtrationthe insoluble ingredients are filtered off
  6. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 8:2:0.2)

出典と根拠

ORDレコード
ord-c96fea7864a94beb8b410c4ef128d374
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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