Cesium fluoride → Methyl 5-methyl-2-(pyridin-2-yl)benzoate

HRID 60907

反応式

HRID 60907 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC.[F-].[Cs+]>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.[Cu]I>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 15110996Methyl 2-bromo-5-methylbenzoate

生成物 1

HCID 67982793Methyl 5-methyl-2-(pyridin-2-yl)benzoate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of methyl 2-bromo-5-methylbenzoate (0.629 g, 2.747 mmol), 2-(tributylstannyl)pyridine (1.32 g, 3.585 mmol), CsF (0.834 g, 5.494 mmol), Pd(PPh3)4 (0.4 g, 0.27 mmol), and CuI (0.105 g, 0.549 mmol) in DMF (20 mL) was degassed for 10 min and then heated in the microwave reactor for 30 min at 130° C. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved with EtOAc and then washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by silica gel to obtain the title compound. ESI-MS (m/z): 228 [M+1]+.

後処理

  1. customwas degassed for 10 min
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude was dissolved with EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customto obtain the crude, which
  9. customwas purified by silica gel

出典と根拠

ORDレコード
ord-f5515e795507478b88057ba06393f836
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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