Sulfuric Acid → HCID 67314636, compound

HRID 1011355Notes

Reaction equation

HRID 1011355 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 2h. 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 2h
  6. customThe solid which formed
  7. customis collected

Sources & evidence

ORD record
ord-0798566e85ab462c8bd865c4a799c977
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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