Methanol → 6-fluoro-3-(5-methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1829030Notes

Reaction equation

HRID 1829030 reaction equation
COC1C=C(OC)C=CC=1[CH2:5][N:6](C)[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[C:16]1[C:24]3[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=3)[NH:18][C:17]1=[O:26])[O:11][CH2:10]2.FC(F)(F)C(O)=O.CO>C(Cl)Cl.O>[F:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16](=[C:12]3[C:13]4[C:9](=[CH:8][C:7]([NH:6][CH3:5])=[CH:15][CH:14]=4)[CH2:10][O:11]3)[C:17](=[O:26])[NH:18]2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 696594233-{5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-6-fluoro-1,3-dihydro-indol-2-one

Product 1

HCID 696592046-fluoro-3-(5-methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneYield 76.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (3-{5-[(2,4-dimethoxy-benzyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-6-fluoro-1,3-dihydro-indol-2-one (197 mg, 0.44 mmol) in methylene chloride (10 ml) was added trifluoroacetic acid (1 ml). The mixture was stirred for 30 minutes at room temperature and then evaporated to give a residue. The residue was treated with 50% MeOH in water (25 ml, containing 1 ml of triethylamine) with heating for 30 minutes. After filtered and dried under vacuum, the resulting solid was mixed with acetone (50 ml), and heated at 50° C. for 30 minutes. The mixture was cooled to room temperature and filtered. The filtrate solution was concentrated under reduced pressure to give a crude product. Trituration of the crude product with CHCl3/hexanes afforded 6-fluoro-3-(5-methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow solid (100 mg, 76%).

Workup

  1. customevaporated
  2. customto give a residue
  3. temperaturewith heating for 30 minutes
  4. filtrationAfter filtered
  5. customdried under vacuum
  6. additionthe resulting solid was mixed with acetone (50 ml)
  7. temperatureheated at 50° C. for 30 minutes
  8. temperatureThe mixture was cooled to room temperature
  9. filtrationfiltered
  10. concentrationThe filtrate solution was concentrated under reduced pressure
  11. customto give a crude product

Sources & evidence

ORD record
ord-f1f1cca7a3b047649a8425d275cee452
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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