2,3-Difluorophenylacetic acid → HCID 178520266、化合物

HRID 269519ノート

反応式

HRID 269519 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25](C(OCC)=O)=[N:24]1.N1C2=NC=CC=C2C(C(OC(C)C)=O)=N1>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:25]1[C:26]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[NH:23][N:24]=1)=[O:12]

参加物

6

反応物 4

HCID 5207722,3-Difluorophenylacetic acidHCID 2733832Lithium HexamethyldisilazideHCID 178459485HCID 178459485、化合物HCID 178470482Ethyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate

生成物 1

HCID 178520266HCID 178520266、化合物収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of 2,3-difluorophenylacetic acid (236 mg, 1.4 mmol) in THF at OC was added 3.85 mL (3.85 mmol) of a solution of lithium bis-trimethylsilylamide in THF. The resulting solution was then added to solution of a 2:1 mixture of ethyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate and isopropyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (104 mg, 0.55 mmol) in THF. The resulting mixture was heated at 75C for 3 hours. The reaction progress was monitored by TLC and HPLC and quenched with saturated NH4Cl, diluted with EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated to give 137 mg (91% yield) of 2-(2,3-difluorophenyl)-1-(1H-pyrazolo[3,4-b]pyridin-3-yl)ethanone. LC-MS Rt=3.3 min ES+ (274.0) ES− (272.1).

後処理

  1. customquenched with saturated NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7c485fca78ec40f4b6af520267262c41
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

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