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Potassium Phosphate, Tribasic → 4-(5-fluoro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1522007
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인쇄 미리보기

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HRID 1522007 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=[C:10]([C:11]#[N:12])[C:3]=12.[F:21][C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26](B(O)O)[CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.O.[Cl-].[Na+].O>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:31][CH3:32])=[C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=[C:10]([C:11]#[N:12])[C:3]=23)[CH:23]=1
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참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 591458241H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

생성물 1

HCID 904136554-(5-fluoro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매
HCID 57417360Sodium chloride; water용매

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온도
60 °C

실험 절차

A mixture of Example 248A (3.0 g, 9.78 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (2.5 g, 14.6 mmol), phenylallylchloro(1,3-bis(diisopropylphenyl)-2-imidazol-2-yliden)palladium(II) (0.19 g, 0.29 mmol) and potassium phosphate (4.1 g, 19.6 mmol) in tetrahydrofuran (60 mL) and water (18 mL) was purged with nitrogen and heated at 60° C. for 3 hours. The mixture was treated with brine, extracted with ethyl acetate (three times) and the organic layer was dried over sodium sulfate. Filtration, concentration and purification by flash chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane) afforded the title compound. MS (ESI+) m/z 398 (M+H)+.

후처리

  1. extractionextracted with ethyl acetate (three times)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationFiltration, concentration and purification by flash chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-790ec83c114f451bb7b948d8d9bf6a1e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073922B2

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