Hydrochloric Acid → 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

HRID 873321ノート

反応式

HRID 873321 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[CH3:12][NH:13][O:14][CH3:15].Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:9])=[N:6][CH:7]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 14232N,O-DimethylhydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210758725-Bromo-3-fluoropyridine-2-carboxylic acid

生成物 1

HCID 210758695-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-Bromo-3-fluoropicolinic acid (1.4 g, 6.5 mmol), N,O-dimethylhydroxylamine.HCl (0.82 g, 8.45 mmol), (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (3.2 g, 8.45 mmol) and triethylamine (2.3 mL, 16.3 mmol) were stirred in DMF (30 mL) at room temperature for 1 d. EtOAc and sat. aq. Na2CO3 solution was added and the aqueous phase extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with 20-80% EtOAc in isohexane to afford 5-bromo-3-fluoro-N-methoxy-N-methylpicolinamide.

後処理

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with 20-80% EtOAc in isohexane

出典と根拠

ORDレコード
ord-df5bd44246d84c3a9b430adaa880ce09
出典データセット
uspto-grants-2015_03
特許番号
US08975406B2

反応ノート

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