Sulfuric Acid → HCID 67314636, compound

HRID 1254099Notes

Reaction equation

HRID 1254099 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+].[CH3:22][O:23][CH:24]([O:36][CH3:37])[CH2:25][C:26]1[N:31]=[C:30]2[CH2:32][O:33][C:34](=O)[C:29]2=[CH:28][CH:27]=1.OS(O)(=O)=O>C1COCC1>[CH3:37][O:36][CH:24]([O:23][CH3:22])[CH2:25][C:26]1[N:31]=[C:30]2[CH2:32][O:33][C:34](=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]3=[O:11])[C:29]2=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 2733832Lithium HexamethyldisilazideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 58478790HCID 58478790, compound

Product 1

HCID 67314636HCID 67314636, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (141 mg, 0.93 mmol.) in THF (4 mL) is treated with a solution of lithium bis(trimethylsilyl)amide (1.9 mL of a 1 M solution in THF, 1.9 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 2-(2,2-dimethoxy-ethyl)-7H-furo[3,4-b]pyridin-5-one (104 mg, 0.47 mmol in THF (1 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 1.5 h and is then poured into cold aqueous 2N H2SO4 solution (10 mL) at 0° C. The resulting mixture is heated at 45° C. for 30 min and then cooled to room temperature and stirred overnight. The reaction mixture is poured into ice water (150 mL) and stirred for 2 h. The solid which formed is collected to give the title compound as a brown solid (76 mg, 46%).

Workup

  1. stirringThe resulting solution is stirred for 1.5 h
  2. temperatureThe resulting mixture is heated at 45° C. for 30 min
  3. temperaturecooled to room temperature
  4. stirringstirred overnight
  5. stirringstirred for 2 h
  6. customThe solid which formed
  7. customis collected

Sources & evidence

ORD record
ord-867c5477ca734e24a8a7d8ada64d0026
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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