Potassium Carbonate → HCID 18671676, compound

HRID 1057612Notes

Reaction equation

HRID 1057612 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[C:10]([F:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]#[N:32]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:30][C:31]#[N:32])[C:15]=2[C:14]2[C:9]1=[C:10]([F:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 18671697HCID 18671697, compound

Product 1

HCID 18671676HCID 18671676, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-benzyl-8-fluoro-9H-carbazol-4-ol (1.0775 g, 0.0037 mol), potassium carbonate (0.6284 g, 0.0046 mol), bromoacetonitrile (0.6 mL, 0.0086 mol) and DMF (12 mL) is stirred at room temperature for 4 h. The mixture is then partitioned between water and dichloromethane. The aqueous layer is also washed with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated to a residue, which is then partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to a residue. The resulting residue is chromatographed on silica gel (100 mL) using ethyl acetate/hexane (20/80) followed by dichloromethane (100 %). The solids are recrystallized from ethyl acetate/heptane to give 0.8869 g (73%) of the title compound; mp 134-134.25° C.; MS (ESI+) for C21H15FN2O m/z 353.1 (M+Na)+; IR(drift) 1578, 1500, 1458, 1439, 1369, 1344, 1335, 1323, 1278, 1235, 1144, 1080, 793, 739, 695 cm−1; 1H NMR (CDCl3) δ5.05, 5.71, 6.75, 7.16, 7.24, 7.41, 8.07. Anal. Calcd for C21H15FN2O: C, 76.35; H, 4.58; N, 8.48. Found: C, 76.15; H, 4.63; N, 8.35.

Workup

  1. customThe mixture is then partitioned between water and dichloromethane
  2. washThe aqueous layer is also washed with ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated to a residue, which
  5. customis then partitioned between water and ethyl acetate
  6. dry with materialThe combined organic layers are dried over magnesium sulfate
  7. concentrationconcentrated to a residue
  8. customThe resulting residue is chromatographed on silica gel (100 mL)
  9. customThe solids are recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-8ef03391abbc47b0b1509fb8c41b8605
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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