Dibromomethane → HCID 21250649, 화합물

HRID 1531811노트

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HRID 1531811 반응식
BrCBr.Cl[Si](C)(C)C.I[CH:10]1[CH2:13][CH2:12][N:11]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].I[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN(C=O)C.[Zn].[O-]S([O-])(=O)=O.[Zn+2]>[CH:26]([C:25]1[CH:28]=[CH:29][C:22]([CH:13]2[CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)=[CH:23][CH:24]=1)=[O:27]

참가 물질

9

반응물 5

HCID 3024DibromomethaneHCID 6397ChlorotrimethylsilaneHCID 966574-IodobenzaldehydeHCID 521585Tris(furan-2-yl)phosphaneHCID 21250577HCID 21250577, 화합물

생성물 1

HCID 21250649HCID 21250649, 화합물

시약·촉매·용매 3

HCID 23994Zinc촉매2회HCID 24424Zinc Sulfate촉매HCID 6228Dimethylformamide용매4회

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온도
70 °C

실험 절차

Zinc dust (253 mg) was stirred under nitrogen overnight. To this was added DMF (5 ml) and dibromomethane (55 mg) dissolved in DMF (1 ml) and the mixture warmed to ˜70° C. The reaction mixture was cooled to room temperature and chlorotrimethylsilane (32 mg) in DMF (1 ml) added and stirred at room temperature for 15 minutes. To this was added 2-iodo-N-Boc-azetidine (Billotte, S., Synlett, 1998, 379-380) (1.04 g) in DMF (5 ml). The reaction mixture warmed to 40° C. and the mixture sonicated for 30 minutes during which time the zinc powder dissolved to leave a hazy solution. To the solution of zincate was added 4-iodobenzaldehyde (Preparation 43) (851 mg in 5 ml DMF), tri-2-furylphosphine (35 mg in 1 ml DMF) and Pd(dbq)2 (42 ml in 1 ml DMF). The resulting mixture was heated at 60-70° C. for 4 hours, cooled to room temperature and partitioned between ammonium chloride solution and diethyl ether, and the aqueous layer was extracted with diethyl ether (3×). The combined organic extracts were dried (Na2SO4), evaporated in vacuo and purified over silica (pentane:ethyl acetate; 4:1) to afford the title compound as a mobile oil, 626 mg.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe reaction mixture warmed to 40° C.
  3. dissolutiondissolved
  4. customto leave a hazy solution
  5. temperatureThe resulting mixture was heated at 60-70° C. for 4 hours
  6. temperaturecooled to room temperature
  7. custompartitioned between ammonium chloride solution and diethyl ether
  8. extractionthe aqueous layer was extracted with diethyl ether (3×)
  9. dry with materialThe combined organic extracts were dried (Na2SO4)
  10. customevaporated in vacuo
  11. custompurified over silica (pentane:ethyl acetate; 4:1)

출처 및 근거

ORD 기록
ord-323e4c0949d04e15b5122a2b3f798784
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200978B1

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