Sodium Carbonate → HCID 89555358, compound

HRID 2203409Notes

Reaction equation

HRID 2203409 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:25]=1.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([OH:36])=[C:31](B(O)O)[CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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:26][C:27]1[CH:32]=[CH:31][C:30]([OH:36])=[C:29]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][N:8]=[C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:6]=3[CH:25]=2)[CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)HCID 58005640HCID 58005640, compound

Product 1

HCID 89555358HCID 89555358, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of di-tert-butyl (5-bromo-1,2-benzoxazol-3-yl)imidodicarbonate (3.9 g, 9.3 mmol) in dimethoxyethane (100 mL) was added (5-chloro-2-hydroxyphenyl)boronic acid (1.6 g, 9.3 mmol), tetrakis(triphenylphosphine)palladium (1.1 g, 0.9 mmol) and 2 M aqueous sodium carbonate (9.3 mL, 18.6 mmol). The mixture was heated at reflux for 5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (75 mL), washed with water (2×40 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 10-50% gradient of ethyl acetate in hexanes to afford di-tert-butyl [5-(5-chloro-2-hydroxyphenyl)-1,2-benzoxazol-3-yl]imidodicarbonate as a colorless solid in 63% yield (2.69 g): 1H NMR (300 MHz, DMSO-d6) δ7.66 (m, 2H), 7.47-7.45 (s, 1H), 7.22-7.19 (m, 3H), 6.90-6.87 (m, 1H), 1.41 (s, 18H); MS (ES+) m/z 460.9 (M+1), 462.9 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate (75 mL)
  5. washwashed with water (2×40 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluting with a 10-50% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e2ac53447ec54051b634162e09878a21
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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