Methanol → 2-Methoxy-1-[1,8]naphthyridin-4-yl-ethanone

HRID 2374171Notes

Reaction equation

HRID 2374171 reaction equation
I(C1C=CC=CC=1)=O.B(F)(F)F.C[Si](C)(C)[O:15][C:16]([C:18]1[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1)=[CH2:17].[CH3:30][OH:31]>>[CH3:30][O:31][CH2:15][C:16]([C:18]1[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1)=[O:17]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 6356Boron trifluorideHCID 92125IodosylbenzeneHCID 685321024-(1-Trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine

Product 1

HCID 685293952-Methoxy-1-[1,8]naphthyridin-4-yl-ethanone

Procedure

To a suspension of iodosobenzene (347 mg, 1.57 mmol), in MeOH (7.2 ml) in an ice bath was added borontrifluoride diethyletherate (0.200 ml, 1.57 mmol) followed by 4-(1-trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine from Step 1 (350 mg, 1.43 mmol) in minimum amount of MeOH. The reaction mixture was warmed to RT overnight and then quenched with solid NaHCO3 and diluted with water. Iodobenzene was extracted with EtOAc and the desired material re-extracted with DCM 2×. The organic layers were dried over Na2SO4 and concentrated to an orange oil (110 mg), which consisted of a 2:3 mixture of starting material and desired title compound. MS (ESI+) for m/z 203 (M+H)+.

Workup

  1. customquenched with solid NaHCO3
  2. additiondiluted with water
  3. extractionIodobenzene was extracted with EtOAc
  4. extractionthe desired material re-extracted with DCM 2×
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated to an orange oil (110 mg), which
  7. additionconsisted of a 2:3 mixture of starting material and desired title compound

Sources & evidence

ORD record
ord-a590e0d18dd84878a57a2ce4951ea1f7
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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