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Allyltributylstannane → 2-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229323
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HRID 2229323 반응식
Br[C:2]1[CH:21]=[N:20][C:5]2[N:6]([CH2:18][CH3:19])[C:7]3[N:15]=[C:14]([Cl:16])[CH:13]=[C:12]([CH3:17])[C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:14]1[CH:13]=[C:12]([CH3:17])[C:8]2[NH:9][C:10](=[O:11])[C:4]3[CH:3]=[C:2]([CH2:24][CH:23]=[CH2:22])[CH:21]=[N:20][C:5]=3[N:6]([CH2:18][CH3:19])[C:7]=2[N:15]=1
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참가 물질

5

반응물 2

HCID 90628AllyltributylstannaneHCID 184666018-Bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

생성물 1

HCID 184666152-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one수율 71.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

A solution of 8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (12.6 g, 34.3 mmol) in DMF (25-0 mL) was degassed under reduced pressure for 20 min. Pd(PPh3)4 (775 mg, 0.7 mmol) was then added followed by allyltributyltin (12.5 mL, 41.1 mmol). After degassing under reduced pressure for 10 min, the mixture was heated to 100° C. for 7 h. The mixture was then concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 19:1) to give the title compound (8.04 g, 71% yield) as a yellow solid.

후처리

  1. customAfter degassing under reduced pressure for 10 min
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (hexane:EtOAc, 19:1)

출처 및 근거

ORD 기록
ord-ea34600dd94e4ccbbb35ca199c51fa6e
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06420359B1

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