Sodium Bicarbonate → HCID 59264723, compound

HRID 646472Notes

Reaction equation

HRID 646472 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([CH3:29])[C:25]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)=[O:32].C(=O)([O-])O.[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([CH3:29])[C:25]=1[C:37]1[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=1)[CH:31]=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343563-Formylphenylboronic acidHCID 59264778HCID 59264778, compound

Product 1

HCID 59264723HCID 59264723, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-iodo-3-methyl-isoxazole (200 mg, 0.38 mmol), and 3-formylbenzene boronic acid (85 mg, 1.5 equiv.) were dissolved in DMF (12 ml) before 1M Sodium hydrogen carbonate solution (1.1 ml, 3.0 equiv) and Pd(Ph3P)2Cl2 (21 mg, 0.08 equiv.) were added with stirring. The reaction mixture was transferred to three microwave tubes which were sealed and the mixtures within degassed before being irradiated by an initial power of 200 W to a temperature of 150° C. for 15 minutes in a CEM microwave apparatus. Upon cooling the reaction mixtures were combined and partitioned between ethyl acetate (10 ml) and water (10 ml). The aqueous layer was separated and extracted again with ethyl acetate (10 ml). The organics were then combined washed with water (2×20 ml), brine (20 ml), dried over Na2SO4 before being condensed in vaccuo and purified by flash chromatography on silica gel, eluting with 25% ethyl acetate in hexane.

Workup

  1. additionwere added
  2. customwere sealed
  3. customthe mixtures within degassed
  4. custombefore being irradiated by an initial power of 200 W to a temperature of 150° C. for 15 minutes in a CEM microwave apparatus
  5. temperatureUpon cooling
  6. customthe reaction mixtures
  7. custompartitioned between ethyl acetate (10 ml) and water (10 ml)
  8. customThe aqueous layer was separated
  9. extractionextracted again with ethyl acetate (10 ml)
  10. washThe organics were then combined washed with water (2×20 ml), brine (20 ml)
  11. dry with materialdried over Na2SO4
  12. customcondensed in vaccuo
  13. custompurified by flash chromatography on silica gel
  14. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-880aaa38723740a7bb8ab0229aed9156
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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