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

HRID 2356085노트

반응식

HRID 2356085 반응식
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

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27348955-Bromo-2-methoxypyridineHCID 22730486HCID 22730486, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-f9e1129b6ee84edfbdabbbb88e4b1838
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754886B2

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