Sodium Carbonate → HCID 67497574, compound

HRID 1628302Notes

Reaction equation

HRID 1628302 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2[CH2:7][CH2:8][NH:9][C:10]=2[CH:11]=1.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[N:16]1[CH:21]=[CH:20][C:19]([C:3]2[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]3[CH2:7][CH2:8][NH:9][C:10]=3[CH:11]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 72207945HCID 72207945, compound

Product 1

HCID 67497574HCID 67497574, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

To a 100 ml flask was added methyl 6-bromoindoline-4-carboxylate 54.1.B (2000 mg, 7.8 mmole), 4-pyridylboronic acid (1152 mg, 9.4 mmole, available from Maybridge), tetrakis(triphenylphosphine)palladium (1805 mg, 1.6 mmole, available from Strem), 30 ml of DMF and 10 ml of saturated sodiumcarbonate. The reaction was stirred at 70° C. for 18 hours at which time additional tetrakis(triphenylphosphine)palladium (900 mg, 0.8 mmole) was added. After an additional 12 hours, the reaction mixture was partitioned between 1000 ml EtAc and 300 ml of water. The organic solvent was removed by rotary evaporation to give methyl 6-(pyridin-4-yl)indoline-4-carboxylate 54.1.C (1986 mg, 100% yield) which was used with no further purification.

Workup

  1. additionwas added
  2. customthe reaction mixture was partitioned between 1000 ml EtAc and 300 ml of water
  3. customThe organic solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-0ab59c2038594397a0e5c2374efd2527
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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