Sodium Carbonate → HCID 59053714, compound

HRID 875048Notes

Reaction equation

HRID 875048 reaction equation
O1CCOCC1.I[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10](C(OC(C)(C)C)=O)[C:9]=1[CH3:24].[CH:25]1[C:34]2[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[C:29]=2[CH:28]=[CH:27][N:26]=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].ClCCl.O>[CH3:24][C:9]1[NH:10][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]=1[C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:29]=1[CH:28]=[CH:27][N:26]=[CH:25]2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 599474Isoquinoline-5-boronic acidHCID 682964281H-Pyrrolo[2,3-b]pyridine-1-carboxylic acid, 3-iodo-2-methyl-, 1,1-dimethylethyl ester

Product 1

HCID 59053714HCID 59053714, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5 ml of dioxane and 0.5 ml of water are added to a mixture, kept under argon, of 179 g (0.5 mmol) of tert-butyl 3-iodo-2-methyl-1H-pyrrolo[2,3-b]-pyridine-1-carboxylate, 87 mg (0.5 mmol) of isoquinoline-5-boronic acid, 159 mg (1.5 mmol) of sodium carbonate and 57 mg (0.05 mmol) of [1,1′bis(diphenylphosphino)ferrocene]palladium(II) dichloride/dichloromethane adduct. The mixture is stirred at 100° C. in a sealed vessel for 26 hours. The reaction mixture is cooled to room temperature, evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: 5-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoquinoline as colourless solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customevaporated
  3. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-70d7cdbba8be4427939b4b4b848bf6bc
Source dataset
uspto-grants-2015_03
Patent number
US08981101B2

Reaction notes

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