Hydrochloric Acid → HCID 67314553, compound

HRID 1011358Notes

Reaction equation

HRID 1011358 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.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:22]([C:24]1[N:29]=[C:28]2[CH2:30][O:31][C:32](=O)[C:27]2=[CH:26][CH:25]=1)=[CH2:23].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:32]1[C:27]2[C:28](=[N:29][C:24]([CH:22]=[CH2:23])=[CH:25][CH:26]=2)[CH2:30][O:31]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 58478753HCID 58478753, compound

Product 1

HCID 67314553HCID 67314553, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (1.13 g, 7.44 mmol) in THF (70 mL) is placed under an Argon atmosphere and cooled in an ice bath. A solution of lithium bis(trimethylsilyl)amide (14.9 mL of a 1.0 M solution in THF, 14.9 mmol) is added slowly at 0° C. and the resulting solution is stirred for 10 min. Solid 2-vinyl-7H-furo[3,4-b]pyridin-5-one (600 mg, 3.72 mmol) is added in one portion. The reaction mixture is stirred for 4.5 h and then poured into an aqueous 1N HCl solution (150 mL). The resulting mixture is stirred at room temperature for 70 h during which time a yellow solid precipitated from solution. The solid is collected by filtration and washed with aqueous 10% HCl solution, MeOH (3×5 mL) and Et2O (3×5 mL). The solid is dried under vacuum overnight to give the title compound (260 mg, 24%).

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction mixture is stirred for 4.5 h
  3. stirringThe resulting mixture is stirred at room temperature for 70 h during which time a yellow solid
  4. customprecipitated from solution
  5. filtrationThe solid is collected by filtration
  6. washwashed with aqueous 10% HCl solution, MeOH (3×5 mL) and Et2O (3×5 mL)
  7. customThe solid is dried under vacuum overnight

Sources & evidence

ORD record
ord-7301d00742bd43dbbaa2860e52783242
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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