Water → 6-Fluoro-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

HRID 1582385ノート

反応式

HRID 1582385 の反応式
[Cl-].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Zn+].Br[C:10]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[C:14]([F:22])[C:11]=1[C:12]#[N:13].O>C1COCC1.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>[F:22][C:14]1[C:11]([C:12]#[N:13])=[C:10]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=1

参加物

7

反応物 3

HCID 962WaterHCID 227212132-Bromo-6-fluoro-3,4-dimethoxybenzonitrileHCID 178479831HCID 178479831、化合物

生成物 1

HCID 98138056-Fluoro-3,4-dimethoxy-2-(2-pyridyl)benzonitrile収率 94.5%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
98 °C

実験手順

A mixture of pyridyl zinc chloride (max 31.5 mmol, prepared from 2-bromopyridine by bromine to magnesium to zinc exchange) in THF (30 ml) and 2-bromo-6-fluoro-3,4-dimethoxybenzonitrile (prepared according to step (d), 3.30 g, 12.7 mmol) in DMF (75 ml) was charged with tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51 mmol), warmed to 98° C. and maintained at this temperature for 15 hours. After this time, the reaction mixture was cooled to room temperature and water (300 ml) added. The resulting mixture was extracted with ethyl acetate (3×150 ml), and the combined organics dried over MgSO4 before being concentrated in vacuo. The crude product was purified on silica gel (eluting with hexane/ethyl acetate [7/3 followed by 1/1] to give 3.1 g of the title product (93%).

後処理

  1. temperaturemaintained at this temperature for 15 hours
  2. temperatureAfter this time, the reaction mixture was cooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×150 ml)
  4. dry with materialthe combined organics dried over MgSO4
  5. concentrationbefore being concentrated in vacuo
  6. customThe crude product was purified on silica gel (
  7. washeluting with hexane/ethyl acetate [7/3 followed by 1/1]

出典と根拠

ORDレコード
ord-2be419c3b1b049248d08cee6e83eefc6
出典データセット
uspto-grants-2004_05
特許番号
US06734303B2

反応ノート

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