2,6-Lutidine → 4-(1-Trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine

HRID 2374170Notes

Reaction equation

HRID 2374170 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([C:11](=[O:13])[CH3:12])=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.O([Si:30]([CH3:33])([CH3:32])[CH3:31])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:31][Si:30]([CH3:33])([CH3:32])[O:13][C:11]([C:4]1[C:5]2[C:10](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)=[CH2:12]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 445974981-[1,8]Naphthyridin-4-ylethanone

Product 1

HCID 685321024-(1-Trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[1,8]Naphthyridin-4-yl-ethanone from Preparation 18 (250 mg, 1.45 mmol), 2,6-lutidine (0.254 ml, 2.18 mmol) in DCM (3.6 ml) was treated with trimethylsilyl triflate (0.276 ml, 1.53 mmol) and allowed to stir at RT overnight. Mixture diluted with DCM and washed with satd. NaHCO3. Organics dried over Na2SO4 and concentrated, furnished 350 mg 4-(1-trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine as an oil. MS (ESI+) for m/z 245 (M+H)+.

Workup

  1. washwashed with satd
  2. dry with materialOrganics dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-450ee955abe94bb2b3b108dad300cb2b
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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