Hydrochloric Acid → HCID 67314523, compound

HRID 1011368Notes

Reaction equation

HRID 1011368 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][CH2:30][C:31]2[N:36]=[C:35]3[CH2:37][O:38][C:39](=O)[C:34]3=[CH:33][CH:32]=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:39]1[C:34]2[C:35](=[N:36][C:31]([CH2:30][CH2:29][CH2:28][N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[CH:32][CH:33]=2)[CH2:37][O:38]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 58478843HCID 58478843, compound

Product 1

HCID 67314523HCID 67314523, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (190 mg, 1.26 mmol.) in THF (1 mL) is placed under an argon atmosphere cooled in an ice bath. A solution of lithium bis(trimethylsilyl)amide (4 mL of a 1M in THF, 4 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-(3-Morpholin-4-yl-propyl)-7H-furo[3,4-b]pyridin-5-one (220 mg, 0.84 mmol) in THF (15 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4.5 h and then poured into an aqueous 10% HCl solution (50 mL). The resulting solution is stirred for 70 h at room temperature. The solid which precipitated from solution is collected by filtration and washed sequentially with small volumes of MeOH, EtOAc, and Et2O and dried under vacuum give the title compound (110 mg, 33%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice-bath is then removed
  3. stirringThe resulting solution is stirred for 4.5 h
  4. stirringThe resulting solution is stirred for 70 h at room temperature
  5. customThe solid which precipitated from solution
  6. filtrationis collected by filtration
  7. washwashed sequentially with small volumes of MeOH, EtOAc, and Et2O
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8e8f90ec68b242c08afd89deae97612f
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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