5-Bromo-2-methoxypyridine → 5-(3,4-Dimethoxyphenyl)-2-methoxypyridine

HRID 2257064

반응식

HRID 2257064 반응식
C[Sn](C)(C)[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][N:18]=1>CN(C)C=O.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>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[N:18][CH:19]=2)[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

참가 물질

5

반응물 2

HCID 27348955-Bromo-2-methoxypyridineHCID 112435354-Trimethylstannylveratrole

생성물 1

HCID 187885605-(3,4-Dimethoxyphenyl)-2-methoxypyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A solution of 2.00 g (6.64 mmol) of 4-trimethylstannylveratrole, 2.49 g (13.2 mmol) of 2-methoxy-5-bromopyridine and 370 mg (0.332 mmol) of Pd (PPh3)4 in 30 mL of dry dimethylformamide is flushed thoroughly with nitrogen and heated to 90° C. for 12 hours. The reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL). The aqueous layer is back extracted with ethyl acetate (100 mL) and the combined organics are washed with brine (75 mL), dried (MgSO4) and evaporated to give a crude yellow oil. The oil is chromatographed on silica gel (eluting with 95:5 hexane/ethyl acetate and then with 9:1 hexane/ethyl acetate) which gives 5-(3,4-dimethoxy-phenyl)-2-methoxypyridine (m.p 83°-84° C.)

후처리

  1. customThe reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL)
  2. extractionThe aqueous layer is back extracted with ethyl acetate (100 mL)
  3. washthe combined organics are washed with brine (75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a crude yellow oil
  7. customThe oil is chromatographed on silica gel (
  8. washeluting with 95:5 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-d9e7de0b9dcf410c997e14a16ad79946
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656643

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