Sodium Carbonate → HCID 22730175, compound

HRID 2085728Notes

Reaction equation

HRID 2085728 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.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>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:28]4[CH:29]=[CH:30][C:25]([C:23]([O:22][CH2:20][CH3:21])=[O:24])=[CH:26][CH:27]=4)=[CH:3][CH:4]=3)[O:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 22730317HCID 22730317, compound

Product 1

HCID 22730175HCID 22730175, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of Example 186B (140 mg, 0.45 mmol) in ethylene glycol dimethyl ether (7.0 mL) at room temperature was treated with tetrakis(triphenylphosphine)palladium (26 mg, 0.02 mmol), stirred for 5 minutes, treated with a solution of Example 186A (104 mg, 0.54 mmol) in ethanol (1.5 mL), stirred for 5 minutes, treated with 2M sodium carbonate (1.1 mL, 2.23 mmol), heated to reflux, and stirred for 4 hours. The reaction mixture was cooled to room temperature and concentrated. The concentrate was dissolved in water (20 mL) and extracted with diethyl ether (4×20 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 384 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ8.71 (s, 1H), 8.18-8.16 (m, 2H), 8.09-8.06 (m, 4H), 7.97-7.89 (m, 4H), 7.30-7.28 (m, 2H), 4.35 (q, 2H), 2.34 (s, 3H), 1.35 (t, 3H).

Workup

  1. stirringstirred for 5 minutes
  2. temperatureheated
  3. temperatureto reflux
  4. stirringstirred for 4 hours
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in water (20 mL)
  7. extractionextracted with diethyl ether (4×20 mL)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d59559a62abd404680241251588a6257
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

Loading…