Hydrochloric Acid → HCID 67313546, compound

HRID 1254103Notes

Reaction equation

HRID 1254103 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+].[N:22]1([CH2:28][CH2:29][C:30]2[N:35]=[C:34]3[CH2:36][O:37][C:38](=O)[C:33]3=[CH:32][CH:31]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]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:38]1[C:33]2[C:34](=[N:35][C:30]([CH2:29][CH2:28][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:31][CH:32]=2)[CH2:36][O:37]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 67315614HCID 67315614, compound

Product 1

HCID 67313546HCID 67313546, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (70 mg, 0.46 mmol) in THF (0.6 mL) is placed under an Argon atmosphere and cooled in an ice bath. A solution of lithium bis(trimethylsilyl)amide (1.2 mL of a 1.0 M solution in THF, 1.2 mmol) is added slowly at 0° C. and the resulting solution is stirred for 10 min. The ice-bath is then removed and a solution of 2-(2-morpholin-4-yl-ethyl)-7H-furo[3,4-b]pyridin-5-one (80 mg, 0.32 mmol) in THF (2 mL) and added dropwise to the reaction mixture. The resulting solution is stirred for 4 h and then poured into an aqueous 10% HCl solution (40 mL). The resulting suspension is stirred at room temperature for 48 h. The yellow solid which precipitated from solution is collected by filtration and washed with 10% HCl, MeOH (3×5 mL) and Et2O (3×5 mL), and dried under vacuum overnight to give the title compound (33 mg, 27%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice-bath is then removed
  3. stirringThe resulting solution is stirred for 4 h
  4. stirringThe resulting suspension is stirred at room temperature for 48 h
  5. customThe yellow solid which precipitated from solution
  6. filtrationis collected by filtration
  7. washwashed with 10% HCl, MeOH (3×5 mL) and Et2O (3×5 mL)
  8. customdried under vacuum overnight

Sources & evidence

ORD record
ord-8b3f069dd61243c08f8c4f8c6994a7f2
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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