1,2-Dimethoxyethane → Methyl 4-(6-methoxy-3-pyridinyl)benzoate

HRID 2356085ノート

反応式

HRID 2356085 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([C:20]([OH:22])=[O:21])[CH:12]=1.[F-].[Cs+].[CH3:25]OCCOC>CO.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>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:16]2[CH:15]=[CH:14][C:13]([C:20]([O:22][CH3:25])=[O:21])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27348955-Bromo-2-methoxypyridineHCID 22730486HCID 22730486、化合物

生成物 1

HCID 4674260Methyl 4-(6-methoxy-3-pyridinyl)benzoate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒

実験手順

A mixture of 5-bromo-2-methoxypyridine (2.93 g, 10 mmol), 4-methylcarboxybenzeneboronic acid (1.80 g, 10 mmol), Pd(Ph3P)4 (0.346 g, 0.3 mmol) and CsF (1.52 g, 10 mmol) in DME (60 mL) and methanol (30 mL) was heated to reflux for 18 hours and concentrated. The concentrate was dissolved in water (50 mL) and ethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 3:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/e 278, 280 (M−H)−, (M+H)+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated
  4. dissolutionThe concentrate was dissolved in water (50 mL)
  5. washethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 3:1 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-f9e1129b6ee84edfbdabbbb88e4b1838
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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