Water → HCID 66787594, compound

HRID 1623499Notes

Reaction equation

HRID 1623499 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7](B3OC(C)(C)C(C)(C)O3)=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:20].O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:29]1[CH:30]=[N:31][CH:32]=[C:33]([CH:37]=1)[C:34]([NH2:36])=[O:35]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:29]3[CH:30]=[N:31][CH:32]=[C:33]([CH:37]=3)[C:34]([NH2:36])=[O:35])=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 18085-BromonicotinamideHCID 10340Sodium CarbonateHCID 585476651-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 66787594HCID 66787594, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one, prepared as described in Example 3a (75 mg, 0.26 mmol) in 12-dimethoxyethane (0.7 mL) was added water (0.3 mL) and ethanol (0.2 ml). The solution was then charged with sodium carbonate (27.6 mg, 0.26 mmol) and 5-bromonicotinamide (CAS#28733-43-9, 53.5 mg, 0.26 mmol) and dichlorobis(triphenylphosphine)palladium (II) (CAS#13965-03-2, 9.1 mg, 0.013 mmol). The reaction vessel was sealed and was heated by microwave irradiation at 150° C. for 10 minutes. The reaction mixture was cooled to room temperature, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (methanol-dichloromethane, 0 to 10%) to furnish 5-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-nicotinamide; MS: (ES+) m/z 268 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.16 (s, 3H), 3.63 (s, 2H), 7.11 (d, J=8.8 Hz, 1H), 7.62 (br. s., 1H), 7.69-7.75 (m, 2H), 8.22 (br. s., 1H), 8.42 (t, J=2.0 Hz, 1H), 8.94 (dd, J=18.9, 1.96 Hz, 2H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel flash chromatography (methanol-dichloromethane, 0 to 10%)

Sources & evidence

ORD record
ord-180119052d584b0fa394f626f0f09fbb
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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