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

HRID 2192642
ノート
印刷プレビュー

反応式

HRID 2192642 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 702
Ethanol
溶媒
HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-077d6bf7b17d4a90bae5d8838c62940b
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329732B2

反応ノート

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