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

HRID 2374171노트

반응식

HRID 2374171 반응식
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]

참가 물질

5

반응물 4

HCID 887Methanol2회HCID 6356Boron trifluorideHCID 92125IodosylbenzeneHCID 685321024-(1-Trimethylsilanyloxy-vinyl)-[1,8]-naphthyridine

생성물 1

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

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a590e0d18dd84878a57a2ce4951ea1f7
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462600B2

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