Sodium Carbonate → HCID 69519412, compound

HRID 855052Notes

Reaction equation

HRID 855052 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[Cl:22].[S:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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:22][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[CH2:2][C:25]1[CH:26]=[CH:27][S:23][CH:24]=1)[O:10][CH:9]([C:13]([F:16])([F:15])[F:14])[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acid2×HCID 69517129ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69519412HCID 69519412, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
65 °C

Procedure

The ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 16, Step 3 (2.0 g, 5.0 mmole) was dissolved in DME (10.8 mL). The thien-3-ylboronic acid (127.96 mg, 5.0 mmole) was added to above solution and followed by addition of Pd(PPh3)4 (40 mg). After addition of 2M Na2CO3 (5.0 mL), the reaction was heated to 60-70° C. The color of the reaction changed from yellow to red and back to yellow. The solution was heated to reflux for 2 hrs. Additional 107 mg of thien-3-ylboronic acid and Pd(PPh3)4 (8 mg) were added to above mixture. After 2 hsr, the reaction was diluted with 5 ml of water and extracted with EtOAc. The organic layer was washed with NaHCO3 (sat.) and dried over MgSO4 and filtered. The filtrate was concentrated to afford the title ester. The ester (dark oil) was purified by chromatography eluted with 5 to 10% EtOAc in Hexane to give 620 mg, which had suitable purity to use without further purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 hrs
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with NaHCO3 (sat.)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-498a90a4d3be4026ae197b2020e0c134
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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