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

HRID 263943

反応式

HRID 263943 の反応式
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]

参加物

5

反応物 2

HCID 27348955-Bromo-2-methoxypyridineHCID 112435354-Trimethylstannylveratrole

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

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 mlxture 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.)

後処理

  1. customThe reaction mlxture 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

出典と根拠

ORDレコード
ord-48e75cf6321249818ffd4e2227df1b44
出典データセット
uspto-grants-1997_07
特許番号
US05646153

関連ノート

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