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

HRID 2382144노트

반응식

HRID 2382144 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-64db3a3841334936b8e0cdd681a7944e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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