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Ethanol → N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamide

HRID 1748659
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HRID 1748659 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2([C:26]#[N:27])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)=[O:8].[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:26]([C:16]1([C:13]2[N:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:28]=[C:2]([C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)[CH:3]=[N:4][CH:5]=3)=[CH:15][CH:14]=2)[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][CH2:17]1)#[N:27]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86692599HCID 86692599, 화합물

생성물 1

HCID 86692600N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamide수율 15%

시약·촉매·용매 3

HCID 178419050
HCID 178419050, 화합물
촉매
HCID 962Water용매2회
HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A solution of 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg), 4-fluorophenylboronic acid (63 mg), bis(triphenylphosphine)palladium (II) dichloride (100 mg) and sodium carbonate (636 mg) in a mixture of toluene (5 ml), ethanol (1 ml) and water (1 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give the titled compound (31 mg).

후처리

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with column chromatography

출처 및 근거

ORD 기록
ord-a4c98d12a87c43ab8fc20a8df0efb0bc
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150555B2

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