Sodium Carbonate → HCID 178434366, compound

HRID 1774964Notes

Reaction equation

HRID 1774964 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[N:9][NH:8][C:5]2=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].[NH:18]1[CH:22]=[CH:21][C:20](B(O)O)=[N:19]1>CN(C=O)C.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]>[CH3:11][C:10]1[C:4]2[C:5](=[CH:6][N:7]=[C:2]([C:20]3[NH:19][N:18]=[CH:22][CH:21]=3)[CH:3]=2)[NH:8][N:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 178434364HCID 178434364, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 178434366HCID 178434366, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine from Example 102 (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 1H-pyrazol-3-ylboronic acid (67 mg, 0.6 mmol). The mixture was stirred under argon for 16 h at 80° C. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 103 (15 mg, 15%). 1H NMR (500 MHz, MeOD) δ 8.96 (s, 1H), 8.23 (s, 1H), 7.71 (s, 1H), 6.90 (d, J=1.5, 1H), 2.65 (s, 3H). ESI MS m/z=200.1 (M+1)

Workup

  1. temperatureAfter cooling down
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

Sources & evidence

ORD record
ord-5a0851e1f8ff434eb9fa5f8043d6e8a8
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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