Methyl iodide → Methyl 6-cyano-7-fluoro-4-methylchroman-4-carboxylate

HRID 1021361Notes

Reaction equation

HRID 1021361 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[C:18]([O-])([O-])=O.[K+].[K+].IC.[H-].[Na+]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][C:6]2([CH3:18])[C:14]([O:16][CH3:17])=[O:15])#[N:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

Product 1

HCID 67080420Methyl 6-cyano-7-fluoro-4-methylchroman-4-carboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (from Example 3, Step E; 28 mg, 0.12 mmol) was diluted with acetonitrile (1 mL) followed by the addition of K2CO3 (49 mg, 0.36 mmol) and iodomethane (0.023 mL, 0.36 mmol). The reaction was then heated at 60° C. for 1 hour, then cooled and NaH (8.6 mg, 0.36 mmol) was added. The reaction was deemed complete by LC. The reaction was loaded onto a Biotage 25 samplet and purified running a gradient 5% ethyl acetate/hexane to 100% ethyl acetate/hexane to yield the title compound (10 mg, 34% yield).

Workup

  1. temperaturecooled
  2. custompurified

Sources & evidence

ORD record
ord-3e39654ddf57455ba6873ce4af1ba413
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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