Triethylamine → 5-Methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine

HRID 2382144ノート

反応式

HRID 2382144 の反応式
[CH2:1]([N:4]([C:11]1[C:12](Br)=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)C(=O)C(F)(F)F)[CH:2]=[CH2:3].[Cl-].C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.[Cl-].[Cl-].[Cl-].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:14]1[N:13]=[C:12]2[C:2]([CH3:3])=[CH:1][NH:4][C:11]2=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 748912193-Bromo-3-(N-allyl-N-trifluoroacetyl)amino-6-methoxypyridineHCID 86639386Tetra(n-butylammonium) chloride

生成物 1

HCID 151795865-Methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine収率 99.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-allyl-N-(2-bromo-6-methoxy-pyridin-3-yl)-2,2,2-trifluoro-acetamide (5.54 g, 16.3 mmol), palladium acetate (147 mg, 0.65 mmol), tetra(n-butylammonium) chloride (4.99 g, 17.9 mmol) and triethylamine (3.72 g, 26.8 mmol) in anhydrous DMF (35 mL) is stirred at 10° C. under N2 for an hour. DMF is evaporated off, and the residue is mixed with water (20 mL) and stirred at rt overnight. EtOAc (50 mL) is added. The organic layer is separated, dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 30-70% EtOAc in heptane to afford 5-methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine (2.62 g) as a solid. 1H NMR (300 MHz, CDCl3): δ 2.38 (s, 3H), 4.05 (s, 3H), 6.62 (s, H), 7.12 (s, H), 7.54 (d, H), 7.94 (br, N—H).

後処理

  1. customDMF is evaporated off
  2. additionthe residue is mixed with water (20 mL)
  3. additionEtOAc (50 mL) is added
  4. customThe organic layer is separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. washeluting with 30-70% EtOAc in heptane

出典と根拠

ORDレコード
ord-64db3a3841334936b8e0cdd681a7944e
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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