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

HRID 1916730노트

반응식

HRID 1916730 반응식
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

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidineHCID 534266384-Bromo-2-ethynylthiophene2회

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c96fea7864a94beb8b410c4ef128d374
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

반응 노트

불러오는 중…