2,3-Difluorophenylacetic acid → HCID 178520266, 화합물

HRID 269519노트

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HRID 269519 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 178520266HCID 178520266, 화합물수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c485fca78ec40f4b6af520267262c41
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446199B2

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