Dimethylformamide → HCID 69517155, compound

HRID 855009Notes

Reaction equation

HRID 855009 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][C:14]=1[Cl:20])[O:8][CH:7]([C:21]([F:24])([F:23])[F:22])[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:41](B(CC)CC)[CH3:42]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:41][CH3:42])=[CH:15][C:14]=1[Cl:20])[O:8][CH:7]([C:21]([F:24])([F:23])[F:22])[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 58934969HCID 58934969, compound

Product 1

HCID 69517155HCID 69517155, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To the mixture of 0.3g (0.59 mmol, 1.0 eqv) of ethyl 6-chloro-7-(2-chloro-4-bromophenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate, 0.32 g (2.3 mmol) of potassium carbonate, 68 mg (0.059 mmol ) of tetrakistriphenyl-phosphinepalladium (0), and 2.5 mL of anhydrous DMF under nitrogen was added 0.83 mL (0.83 mmol, 1.0 M in THF) of triethylborane. The mixture was heated to 110° C. and shaken for five hrs. LC-MS indicated that the reaction was completed. After cooling to room temperature, the reaction was added to 50 mL of ethyl acetate. The resulting organic phase was washed with brine three times, and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified on silica gel column with 1:9 EtOAc/hexane to afford 0.23 g (84.7%) of a light yellow solid. The product was used directly in the next step.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe resulting organic phase was washed with brine three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the volatiles
  5. customthe residue was purified on silica gel column with 1:9 EtOAc/hexane

Sources & evidence

ORD record
ord-242e0e8e4e634d2697cd0dc3c9df3115
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…