Dimethylformamide → 1H-Pyrazolo[3,4-C]pyridine-5-carboxaldehyde

HRID 2074478노트

반응식

HRID 2074478 반응식
[Li]C(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[CH:15]=[N:14][NH:13][C:10]2=[CH:11][N:12]=1.CN([CH:19]=[O:20])C>C1COCC1>[NH:13]1[C:10]2=[CH:11][N:12]=[C:7]([CH:19]=[O:20])[CH:8]=[C:9]2[CH:15]=[N:14]1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 596944711H-Pyrazolo[3,4-C]pyridine-5-carboxaldehyde수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

t-BuLi (27 mL, 1.7 M in pentane) was added to 100 mL of THF at −78° C. 5-bromo-1H-pyrazolo[3,4-c]pyridine (3.0 g, 15 mmol) was added dropwise to the solution in 50 ml of THF via addition funnel. The resulting mixture was stirred for 1 h, at which point DMF (6.0 mL, 76 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred 2 h. The reaction was then carefully quenched with aq. NH4Cl and diluted with EtOAc. The resulting biphasic mixture was partitioned in a separatory funnel. The aqueous portion was extracted three tines with EtOAc, and the combined organic extracts were washed with brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (100% CH2Cl2 to 7.5% MeOH/CH2Cl2), afforded the desired 1H-pyrazolo[3,4-c]pyridine-5-carbaldehyde (1.1 g, 50% yield) as a white solid. H1 NMR (MeOD, 400 MHz) keto tautomer: 10.17 (s, 1H), 9.19 (s, 1H), 8.56 (s, 1H), 8.46 (s, 1H); enol tautomer: 9.00 (s, 1H), 8.25 (s, 1H), 8.05 (s, 2H), 5.73 (s, 1H). MS (API-ES) m/z (%): 147 (100%, M++1).

후처리

  1. additionwas added dropwise
  2. customThe reaction was then carefully quenched with aq. NH4Cl
  3. additiondiluted with EtOAc
  4. customThe resulting biphasic mixture was partitioned in a separatory funnel
  5. extractionThe aqueous portion was extracted three tines with EtOAc
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-65241f2614304d309369681a3e254c7c
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919514B2

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