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

HRID 1775082
Notes
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Reaction equation

HRID 1775082 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-8760be28749a4a3ab2141ffe14e8cab4
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes