Sodium Carbonate → 3-(3,4-dihydro-2H-pyran-5-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775082노트

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HRID 1775082 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[NH:4][N:3]=1.[O:17]1[CH2:22][CH2:21][CH2:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[O:17]1[CH:18]=[C:19]([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[C:8]([C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[NH:4][N:3]=2)[CH2:20][CH2:21][CH2:22]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 532171522-(3,4-Dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178506572HCID 178506572, 화합물

생성물 1

HCID 712536513-(3,4-dihydro-2H-pyran-5-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine수율 35%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

In a microwave tube was added 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (0.32 g, 1 mmol), 2-(5,6-dihydro-4H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.31 g, 1.5 mmol), 2 M Na2CO3 (2 mmol, 1 mL), PdCl2(dppf) (87 mg, 0.1 mmol) and dioxane (8 mL). The suspension was purged with N2 and heated under microwave radiation at 130° C. for 1 hour. It was then cooled to room temperature. Solvent was removed under reduced pressure. The residue was purified by SGC (Petrol/EtOAc:5/1 to 1/1) to give 281 as a yellow solid (97 mg, 35%). 1H NMR (400 MHz, DMSO) δ 9.19 (d, J=1.2 Hz, 1H), 9.07 (d, J=0.8 Hz, 1H), 8.53-856 (m, 2H), 8.45 (d, J=0.8 Hz, 1H), 7.71 (s, 1H), 7.47-7.49 (m, 1H), 4.08-4.10 (m, 2H), 2.59-2.61 (m, 2H), 1.98-2.0 (m, 2H). ESI MS m/z=279 (M+1)

후처리

  1. customThe suspension was purged with N2
  2. temperatureIt was then cooled to room temperature
  3. customSolvent was removed under reduced pressure
  4. customThe residue was purified by SGC (Petrol/EtOAc:5/1 to 1/1)

출처 및 근거

ORD 기록
ord-8760be28749a4a3ab2141ffe14e8cab4
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260425B2

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