Methanesulfonic Acid → 6-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 1778772ノート

反応式

HRID 1778772 の反応式
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([I:11])[C:5]2=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CS(O)(=O)=O>C(Cl)Cl.O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:12]3)[N:9]=[C:10]([I:11])[C:5]2=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 178477878HCID 178477878、化合物

生成物 1

HCID 867228676-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine収率 88%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-chloro-3-iodo-1H-pyrazolo[3,4-b]pyridine (0.70 g, 2.5 mmol), dihydropyran (690 μL, 7.5 mmol) and methanesulfonic acid (33 μL, 0.50 mmol) in methylene chloride (30 mL) and tetrahydrofuran (10 mL) in reaction flask was stirred at r.t. overnight. It was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.80 g). LCMS (M-84+H)+=279.9.

後処理

  1. customin reaction flask
  2. concentrationIt was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

出典と根拠

ORDレコード
ord-8183e5d87ed34f47887e223f9904c23b
出典データセット
uspto-grants-2016_02
特許番号
US09266892B2

反応ノート

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