Sodium Bicarbonate → HCID 18433466, compound

HRID 2306189Notes

Reaction equation

HRID 2306189 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)[CH3:16])[CH:13]=[N:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:15]([N:14]2[C:10]([CH2:9][OH:8])=[CH:11][N:12]=[CH:13]2)[CH3:16])=[CH:18][C:19]=1[F:25])#[N:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 10904469HCID 10904469, compound

Product 1

HCID 18433466HCID 18433466, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(tert-butyldimethylsilyloxymethyl)-1-[1-(4-cyano-3-fluorophenyl)ethyl]imidazole, as described above in Step E, (101 mg, 0.281 mmol) in THF (2 mL) was added tetrabutylammonium fluoride (0.309 mL of a 1.0 M solution in THF, 0.309 mmol) dropwise. The reaction mixture was stirred for 1 hour, then poured into saturated aqueous NaHCO3 (20 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2—0% to 10% MeOH, to yield the desired product as a pale solid.

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of CH2Cl2—0% to 10% MeOH

Sources & evidence

ORD record
ord-9a5af442fbab4accb6141553f71ed7f0
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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