Sodium Carbonate → HCID 86649465, compound

HRID 2190914Notes

Reaction equation

HRID 2190914 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].[O:18]([C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCOC(C)=O.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>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:28]1[CH:29]=[CH:30][C:25]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:26][CH:27]=1)[CH:9]=2)=[O:4]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 67523776HCID 67523776, compoundHCID 86649466HCID 86649466, compound

Product 1

HCID 86649465HCID 86649465, compoundYield 68.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-bromo-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (256 mg, 0.855 mmol), 4-phenoxyphenylboric acid (211 mg, 0.984 mmol), Pd(PPh3)4 (99 mg, 0.086 mmol) and aqueous sodium carbonate solution (1.1 mL, 2 M) in 1,2-dimethoxyethane (5 mL) was refluxed for 2.5 h. Then cooled, the slurry was diluted with EtOAc and water, solids were filtered off over Celite; EtOAc phase was separated from aqueous, washed with sat. NaCl solution, dried over sodium sulfate, filtered, and concentrated; the crude material was crystallized from dichloromethane and methanol to give the desired product as white micro crystals (228 mg). 1H NMR (200 MHz, CDCl3): δ (ppm)=14.58 (s, 1H), 8.04 (d, 1H, J=8.4 Hz), 7.61-7.04 (m, 11H), 4.04 (s, 3H).

Workup

  1. temperaturewas refluxed for 2.5 h
  2. temperatureThen cooled
  3. filtrationwere filtered off over Celite
  4. customEtOAc phase was separated from aqueous,
  5. washwashed with sat. NaCl solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe crude material was crystallized from dichloromethane and methanol

Sources & evidence

ORD record
ord-706a26a37b444e6b8719f265eecf02ff
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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