Potassium Carbonate → Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate

HRID 1626391Notes

Reaction equation

HRID 1626391 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[OH:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[C:26]([O:25][C:23]([C:22]1[CH:21]=[CH:20][C:19]([O:18][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:31][CH:30]=1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

Product 1

HCID 67080240Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To methyl 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (3.04 g, 12.9 mmol), tert-butyl 4-hydroxybenzoate (3.10 g, 16.0 mmol) and potassium carbonate (4.47 g, 32.3 mmol) in 20 mL of NMP was added oven dried powdered 4 Angstrom sieves (2.5 gm), the reaction was degassed with argon for 15 minutes then heated at 110° C. overnight. The reaction was diluted with ethyl acetate and water. The organic layer was dried, concentrated and the residue flashed with 4:1 hexanes/ethyl acetate to 3:1 hexanes/ethyl acetate to provide the desired product (2.3 g, 44%).

Workup

  1. customdried
  2. customthe reaction was degassed with argon for 15 minutes
  3. additionThe reaction was diluted with ethyl acetate and water
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00d1f0cca52c41c4a83faa02e8904193
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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