2-Bromo-1,1-dimethoxyethane → 3-Bromo-7-chloro-1,6-naphthyridine

HRID 715097Notes

Reaction equation

HRID 715097 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([Cl:10])[CH:3]=1.[Br:11][CH2:12][CH:13](OC)OC.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>CC#N.CCOC(C)=O>[Br:11][C:12]1[CH:13]=[N:1][C:2]2[C:7]([CH:8]=1)=[CH:6][N:5]=[C:4]([Cl:10])[CH:3]=2

Participants

6

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 2733225Ytterbium triflateHCID 454801984-Amino-6-chloropyridine-3-carbaldehyde

Product 1

HCID 898156613-Bromo-7-chloro-1,6-naphthyridineYield 53.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat a mixture of 4-amino-6-chloronicotinaldehyde (2.00 g, 12.77 mmol), 2-bromo-1,1-dimethoxyethane (6.48 g, 38.3 mmol) and ytterbium(III) trifluoromethanesulfonate (1.981 g, 3.19 mmol) in MeCN (25 mL) at 80° C. overnight. Cool to RT, dilute with EtOAc, collect the solids via filtration, rinse with EtOAc and dry. Wash the filtrate with H2O, then brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex). Combine the two solids to afford the title compound (1.67 g, 53%) as an off-white solid. MS(ESI) m/z: 244.9 (M+H+).

Workup

  1. temperatureHeat
  2. customcollect the solids
  3. filtrationvia filtration
  4. washrinse with EtOAc
  5. customdry
  6. washWash the filtrate with H2O
  7. dry with materialbrine, dry over Na2SO4
  8. concentrationconcentrate to dryness
  9. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-b34321743c6f45a9b4f6f16ac12e0f45
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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