Potassium Carbonate → HCID 69517757, compound

HRID 854921Notes

Reaction equation

HRID 854921 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1.Br[C:17]1[C:26]([Cl:27])=[C:25]([Cl:28])[C:24]([O:29][CH3:30])=[C:23]2[C:18]=1[CH:19]=[C:20]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:21]([C:31]([F:34])([F:33])[F:32])[O:22]2>O1CCOCC1.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>[Cl:27][C:26]1[C:17]([CH3:1])=[C:18]2[C:23](=[C:24]([O:29][CH3:30])[C:25]=1[Cl:28])[O:22][CH:21]([C:31]([F:34])([F:33])[F:32])[C:20]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:19]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 86599468HCID 86599468, compound

Product 1

HCID 69517757HCID 69517757, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Pd(PPh3)4 (0.13 g, 0.85 mmol), K2CO3 (0.34 g, 0.85 mmol) and trimethylboroxine (0.14 g, 0.85 mmol) was added to a stirring solution of ethyl 5-bromo-6,7-dichloro-8-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.38 g, 0.85 mmol) dissolved in 1,4-dioxane and heated to reflux for 24 hrs. Allowed to cool to R.T., filtered through celite and washed with EtOAc. The resulting solution was condensed in vacuo and purified by flash chromatography (silica gel) and eluted with 10% EtOAc/ hexanes to yield 0.18 g (56%) of the title compound as an amorphous solid: GCMS m/z 384.0 (M+). 1H NMR (CDCl3/300 MHz) 7.92 (s, 1H), 5.80 (q, 1H, J=7.0 Hz), 4.35 (m, 2H), 3.89 (s, 3H), 2.47 (s, 3H), 1.36 (m, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hrs
  3. filtrationfiltered through celite
  4. washwashed with EtOAc
  5. customcondensed in vacuo
  6. custompurified by flash chromatography (silica gel)
  7. washeluted with 10% EtOAc/ hexanes

Sources & evidence

ORD record
ord-237aa871b7c64b04a56410b1dbbfb82b
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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