Triphenylphosphine → 2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1765531노트

반응식

HRID 1765531 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH2:23]([CH:27]([Sn])C=C(CCCC)CCCC)[CH2:24]CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:27][CH:23]=[CH2:24])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 120853472-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 86589045Tributylallyltin

생성물 1

HCID 211074042-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide수율 84.4%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

2-Chloro-5-iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (prepared as described in WO 99/29661) (7.74 g), tri-n-butylallyltin (5.99 g), dichlorobis(triphenylphosphine)palladium(II) (1.24 g), triphenylphosphine (1.86 g), lithium chloride (6.11 g) and N,N-dimethylformamide. (260 mL) were heated together under nitrogen from 110° C. to 130° C. over 20 minutes, and then at 130° C. for 25 minutes. The mixture was then cooled, poured into brine (500 mL), extracted into ethyl acetate (3×250 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. The crude mixture was purified by column chromatography eluting with 9:1 isohexane/ethyl acetate to give the sub-titled compound (5.23 g).

후처리

  1. temperature(260 mL) were heated together under nitrogen from 110° C. to 130° C. over 20 minutes
  2. temperatureThe mixture was then cooled
  3. extractionextracted into ethyl acetate (3×250 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe crude mixture was purified by column chromatography
  9. washeluting with 9:1 isohexane/ethyl acetate

출처 및 근거

ORD 기록
ord-609ee50ed6cd4d9d81fd44b804743d4b
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07227038B2

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