Sulfuric Acid → HCID 71114832, compound

HRID 1624037Notes

Reaction equation

HRID 1624037 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[C:11]3[CH:12]=[N:13][N:14](C4CCCCO4)[C:15]=3[CH2:16][CH2:17][CH:18]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].FC1C=C(C2C3C(CCC=2)=NN(C2CCCCO2)C=3)C=CC=1C#N.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.CC#N>[NH:14]1[C:15]2[CH2:16][CH2:17][CH:18]=[C:10]([C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=3)[C:11]=2[CH:12]=[N:13]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 71114808HCID 71114808, compoundHCID 71114816HCID 71114816, compound

Product 1

HCID 71114832HCID 71114832, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-4-(1-tetrahydropyran-2-yl-6,7-dihydroindazol-4-yl)benzonitrile and 2-fluoro-4-(2-tetrahydropyran-2-yl-6,7-dihydroindazol-4-yl)benzonitrile (0.23 g, 0.71 mmol) and H2SO4 (0.08 mL, 1.43 mmol) are added to CH3CN (5.0 mL) and the solution is stirred at room temperature for 6.0 hours. Aqueous Na2CO3 is added to basify the reaction, which is then diluted with ethyl acetate, the layers separated, and the aqueous back extracted with ethyl acetate (3×). The organics are combined, dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified by silica gel flash chromatography eluting with 99:1 CH2Cl2/MeOH to give the title compound (0.102 g, 60%). ES/MS m/z 240 (M+H).

Workup

  1. customthe reaction, which
  2. customthe layers separated
  3. extractionthe aqueous back extracted with ethyl acetate (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by silica gel flash chromatography
  8. washeluting with 99:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-d88213badabc48f9963df36fd2bd6447
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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