Sulfuric Acid → HCID 76798894, compound

HRID 1254100Notes

Reaction equation

HRID 1254100 reaction equation
C[O:2][CH:3](OC)[CH2:4][C:5]1[N:10]=[C:9]2[CH2:11][O:12][C:13](=[C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=4)[NH:16][C:15]3=[O:24])[C:8]2=[CH:7][CH:6]=1.S(=O)(=O)(O)O>C1COCC1>[F:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:24])[C:14]2=[C:13]1[C:8]2[C:9](=[N:10][C:5]([CH2:4][CH:3]=[O:2])=[CH:6][CH:7]=2)[CH2:11][O:12]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67314636HCID 67314636, compound

Product 1

HCID 76798894HCID 76798894, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-[2-(2,2-dimethoxy-ethyl)-7H-furo[3,4-b]pyridin-5-ylidene]-5-fluoro-1,3-dihydro-indol-2-one (52 mg, 0.16 mmol) in THF (5 mL) is treated with 0.63 mL of an aqueous 2.5 M sulfuric acid solution (0.63 mL). The reaction mixture is heated to 60° C. for 1 h, cooled to room temperature and poured into 100 mL ice water with stirring. The brown solid which precipitated is collected by filtration, washed with water, and dried under vacuum to give the title compound as brown solid (27 mg, 54%).

Workup

  1. temperaturecooled to room temperature
  2. customThe brown solid which precipitated
  3. filtrationis collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c7b2a0b4e33a4e2c8567be00eded05ce
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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