Sodium Carbonate → HCID 22561848, compound

HRID 1839810Notes

Reaction equation

HRID 1839810 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:14]/[C:15]1[NH:16][CH:17]=[C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[C:19]=1[CH3:20])/[C:5](=[O:13])[NH:6]2.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd]>[CH3:12][O:11][C:10]1[C:2]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5](=[O:13])/[C:4]/2=[CH:14]\[C:15]1[NH:16][CH:17]=[C:18]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:19]=1[CH3:20]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69891124HCID 69891124, compound

Product 1

HCID 22561848HCID 22561848, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-bromo-5-methoxy-3-[1-[3-methyl-4-(morpholine-4-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one (223 mg, 0.5 mmol) and phenylboronic acid (73 mg, 0.6 mmol) in DME/water (5 mL) were added Palladium catalyst Pd(PPh3)2Cl2 (10.5 mg) and sodium carbonate (106 mg, 1 mmol). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 85° C. oil bath for overnight. TLC showed some de-bromination of the starting material. The degass procedure was repeated for three more times and the heating was continued for 3 more days. The mixture was cooled to room temperature, the unreacted starting material was filtered off and the mother liquor was concentrated. The residue was purified on a silica gel column to give 21 mg of 5-methoxy-3-[1-[3-methyl-4-(morpholine-4-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-phenyl-1,3-dihydro-indol-2-one.

Workup

  1. customThe system was degassed
  2. additioncharged with nitrogen
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationwas filtered off
  5. concentrationthe mother liquor was concentrated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-0333b079b7314995b591672bf1ba5760
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

Loading…