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Diisopropylethylamine → 6-(2,6-Difluorophenyl)-3-fluoro-2-methylpyridine

HRID 1523510
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인쇄 미리보기

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HRID 1523510 반응식
Br[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1B(O)O.CCN(C(C)C)C(C)C>C(O)C.C1(C)C=CC=CC=1.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>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][CH:3]=1
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참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 27343362,6-Difluorophenylboronic acidHCID 27831806-Bromo-3-fluoro-2-methylpyridine

생성물 1

HCID 592265276-(2,6-Difluorophenyl)-3-fluoro-2-methylpyridine수율 88%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 702
Ethanol
용매
HCID 1140Toluene용매

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온도
120 °C

실험 절차

To a solution of 6-bromo-3-fluoro-2-methylpyridine (1.0 equiv.) in ethanol and toluene (1:1, 0.2 M) was added 2,6-difluorophenylboronic acid, DIEA (5 equiv.) and Pd(PPh3)4 (0.2 equiv.). The reaction was heated in the microwave at 120° C. for 30 min. The solution was filtered and rinsed with ethyl acetate. The volatiles were removed in vacuo and the crude was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (2.5-20% ethyl acetate). Upon concentration of the pure fractions, 6-(2,6-difluorophenyl)-3-fluoro-2-methylpyridine was isolated in 88% yield. LC/MS=224.1 (M+H), Rt=0.87 min.

후처리

  1. filtrationThe solution was filtered
  2. washrinsed with ethyl acetate
  3. customThe volatiles were removed in vacuo
  4. customthe crude was purified via silica gel column chromatography
  5. washeluting with ethyl acetate and hexanes (2.5-20% ethyl acetate)

출처 및 근거

ORD 기록
ord-02aa5cf7bcca4d1d9d0eb650e81d81bf
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079889B2

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