Hydrochloric Acid → 3-{5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-6-fluoro-1,3-dihydro-indol-2-one

HRID 1829029Notes

Reaction equation

HRID 1829029 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH3:23][O:24][C:25]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:26]=1[CH2:27][N:28]([CH3:39])[C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34](=O)[O:33][CH2:32]2.Cl.[OH-].[Na+]>C(COC)OC.C1C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:26]=1[CH2:27][N:28]([CH3:39])[C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34](=[C:6]1[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][C:7]1=[O:11])[O:33][CH2:32]2

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 14798Sodium HydroxideHCID 37310136-fluoro-2,3-dihydro-1H-indol-2-oneHCID 22061456HCID 22061456, compoundHCID 178418339Butyllithium

Product 1

HCID 696594233-{5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-6-fluoro-1,3-dihydro-indol-2-oneYield 64%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 6-fluorooxindole (0.60 g, 3.99 mmol) in anhydrous dimethoxyethane (20 ml) under nitrogen was added 2.5M n-BuLi solution in hexane (3.5 ml, 8.75 mmol). After the reaction was stirred at room temperature for 10 minutes, 5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-one (1.0 g, 3.19 mmol) was added. After stirred at room temperature for 2.5 hours, the reaction mixture was poured into 1M HCl aqueous solution (70 ml), and then basified with NaOH aqueous solution. The solid was separated, washed with water, and dried under vacuum to give a crude product. Trituration of the crude product with benzene yielded 3-{5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-6-fluoro-1,3-dihydro-indol-2-one as a yellow solid (0.91 g, 64%).

Workup

  1. stirringAfter stirred at room temperature for 2.5 hours
  2. customThe solid was separated
  3. washwashed with water
  4. customdried under vacuum
  5. customto give a crude product

Sources & evidence

ORD record
ord-b7506ee4997447b8885f85b53b414c8c
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

Loading…