Chlorotrimethylsilane → 6-(2,5-Dimethyl-pyrrol-1-yl)-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

HRID 729757

반응식

HRID 729757 반응식
C[Si](Cl)(C)C.I[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.Br[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]2[C:47]([CH3:48])=[CH:46][CH:45]=[C:44]2[CH3:49])[N:38]=1>O1CCCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([N:43]3[C:47]([CH3:48])=[CH:46][CH:45]=[C:44]3[CH3:49])[N:38]=2)[CH2:8][CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

7

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 521585Tris(furan-2-yl)phosphaneHCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylateHCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

생성물 1

HCID 578328696-(2,5-Dimethyl-pyrrol-1-yl)-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester수율 30.8%

시약·촉매·용매 2

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

After stirring for 3 minutes at 60° C. the reaction medium is left to return to ambient temperature. 0.047 ml of trimethylsilyl chloride is added and stirring is carried out for 30 minutes at ambient temperature. 1 g (3.2mmol) of 2 solubilized beforehand in 2 ml of tetrahydrofuran is added. This reaction mixture is stirred for 45 minutes at ambient temperature and it is added to a solution containing 30 mg (0.032 mmol) of tris(dibenzylideneacetone) dipalladium marketed by Aldrich and 30 mg (0.13 mmol) of tris(2-furyl)phosphine marketed by LANCASTER. Then 1 g (4 mmol) of 3 solubilized beforehand in 10 ml of tetrahydrofuran is added. The reaction mixture is left under magnetic stirring at 60° C. for 2 hours, then left to return to ambient temperature, filtered on clarcel and extracted between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. After extracting the aqueous phase twice with ethyl acetate, the organic phases are combined and dried over magnesium sulphate. The ethyl acetate is evaporated off under reduced pressure (2 kPa) and the crude residue is purified by chromatography on silicagel eluting with a heptane/ethyl acetate mixture 4:1. 350 mg (yield=30%) of expected product is recovered in the form of a yellow oil.

후처리

  1. waitis left
  2. customto return to ambient temperature
  3. stirringstirring
  4. waitis carried out for 30 minutes at ambient temperature
  5. stirringThis reaction mixture is stirred for 45 minutes at ambient temperature
  6. additionit is added to a solution
  7. waitThe reaction mixture is left
  8. stirringunder magnetic stirring at 60° C. for 2 hours
  9. waitleft
  10. customto return to ambient temperature
  11. filtrationfiltered on clarcel
  12. extractionextracted between ethyl acetate
  13. extractionAfter extracting the aqueous phase twice with ethyl acetate
  14. dry with materialdried over magnesium sulphate
  15. customThe ethyl acetate is evaporated off under reduced pressure (2 kPa)
  16. customthe crude residue is purified by chromatography on silicagel
  17. washeluting with a heptane/ethyl acetate mixture 4:1

출처 및 근거

ORD 기록
ord-6b0a9e7e658f40fc8362ceffbdcebf5a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582640B2

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