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

HRID 2374171ノート

反応式

HRID 2374171 の反応式
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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-a590e0d18dd84878a57a2ce4951ea1f7
出典データセット
uspto-grants-2008_12
特許番号
US07462600B2

反応ノート

読み込み中…