Hydrochloric Acid → HCID 67314373, compound

HRID 1011335Notes

Reaction equation

HRID 1011335 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][C:13]1[N:18]=[C:17]2[CH2:19][O:20][C:21](=O)[C:16]2=[CH:15][CH:14]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:21]1[C:16]2[C:17](=[N:18][C:13]([CH3:12])=[CH:14][CH:15]=2)[CH2:19][O:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 58478770HCID 58478770, compound

Product 1

HCID 67314373HCID 67314373, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (752 mg, 4.98 mmol.) in THF (5 mL) is placed under an argon atmosphere and cooled in an ice bath. A solution of Li bis(trimethylsilyl)amide (13.2 mL of a 1M in THF, 13.2 mmol) is added slowly at 0° C. and the resulting solution is stirred at 0° C. for 10 min. The ice-bath is removed and a solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (495 mg, 3.32 mmol) in THF (6 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4.5 h and then poured into 50 mL of aqueous 10% HCl solution. After 10 min at room temperature, the reaction is heated to ˜90° C. for 45 min and is then stirred at room temperature for 36 h. The solid which precipitated from solution is collected by filtration and washed sequentially with small volumes of MeOH (3×5 mL), EtOAc (3×5 mL) and Et2O (3×5 mL) followed by drying to give the title compound as a yellow solid (450 mg, 48%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice-bath is removed
  3. stirringThe resulting solution is stirred for 4.5 h
  4. waitAfter 10 min at room temperature
  5. temperaturethe reaction is heated to ˜90° C. for 45 min
  6. stirringis then stirred at room temperature for 36 h
  7. customThe solid which precipitated from solution
  8. filtrationis collected by filtration
  9. washwashed sequentially with small volumes of MeOH (3×5 mL), EtOAc (3×5 mL) and Et2O (3×5 mL)
  10. customby drying

Sources & evidence

ORD record
ord-b277257833d448128debc83dab646e40
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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