Hydrochloric Acid → 5-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 49505

반응식

HRID 49505 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.[CH2:24]([OH:29])[CH2:25][CH2:26][C:27]#[CH:28].Cl>[Cu]I>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:28]#[C:27][CH2:26][CH2:25][CH2:24][OH:29])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 793464-Pentyn-1-ol2회HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate

생성물 1

HCID 695147945-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester수율 105.9%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

To 3.73 g (12.5 mmol) 5-Bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 25 ml piperidine 722 mg (0.63 mmol) tetrakis-(triphenylphosphine)-palladium and 120 mg (0.625 mmol) CuI were added. The solution was purged with argon and was heated to 80° C. over a period of 45 min, during which 0.9 ml (9.4 mmol) 4-pentynol were added. Additional 0.9 ml (9.4 mmol) 4-pentynol were added and the mixture was stirred for 2 h, poured into ice water and 2M HCl was added. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Purification on silica gel with hexane/EtOAc 4:1 to 2:1 yielded 3.0 g (79%) 5-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as light brown solid, MS: 302 (MH+). (See also: Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Teply, Filip; Saman, David; Fiedler, Pavel. Coupling reactions of halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes. Collect. Czech. Chem. Commun. (1999), 64(4), 649-672)

후처리

  1. customThe solution was purged with argon
  2. additionwere added
  3. additionwas added
  4. extractionThe inorganic phase was extracted with ether
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customPurification on silica gel with hexane/EtOAc 4:1 to 2:1

출처 및 근거

ORD 기록
ord-6c8d6f9217da4f5a9a94383d8c289b19
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706751B2

연결된 노트

불러오는 중…