Water → methyl (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylate

HRID 537924Notes

Reaction equation

HRID 537924 reaction equation
Br[C:2]1[C:6]([CH3:8])([CH3:7])[O:5]/[C:4](=[C:9]2/[C:10](=[O:22])[NH:11][C:12]3[C:17]/2=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=3)/[CH:3]=1.Cl.CC1(C)C(C)(C)OB([C:32]2[CH:44]=[CH:43][C:35]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:34][CH:33]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O>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]>[CH3:7][C:6]1([CH3:8])[O:5]/[C:4](=[C:9]2/[C:10](=[O:22])[NH:11][C:12]3[C:17]/2=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=3)/[CH:3]=[C:2]1[C:32]1[CH:33]=[CH:34][C:35]([CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 467390144-((Morpholino)methyl)phenylboronic acid pinacol ester hydrochlorideHCID 58926238methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate

Product 1

HCID 58926016methyl (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylate

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A mixture of methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate (90 mg, 0.25 mmol), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine hydrochloride (92 mg, 0.27 mol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with CH2Cl2, 20 mg, 0.027 mmol) and 2M Na2CO3 (0.5 mL, 1.0 mmol) in 8 mL of DMF was heated in 85° C. bath under nitrogen for 90 minutes. The mixture was cooled to room temperature and poured into 100 mL of water. The precipitates were filtered, washed with water and dried to give the crude product, which was purified through silica gel column with 1-5% MeOH/CHCl3 to give methyl (3E)-3-{5,5-dimethyl-4-[4-(morpholin-4-ylmethyl)phenyl]furan-2(5H)-ylidene}-2-oxoindoline-5-carboxylate as yellow solid. Yield: 20 mg, 18%.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried
  5. customto give the crude product, which
  6. customwas purified through silica gel column with 1-5% MeOH/CHCl3

Sources & evidence

ORD record
ord-3e7e15fc24f4414db4de8c4bda09f537
Source dataset
uspto-grants-2014_10
Patent number
US08865682B2

Reaction notes

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