Triethylamine → HCID 57962099, compound

HRID 541581Notes

Reaction equation

HRID 541581 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[CH:13]([C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][CH:20]=1)=[CH2:14].C(N(CC)CC)C.C(OCC)(=O)C>CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].CN(C)C=O.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2](/[CH:14]=[CH:13]/[C:15]2[CH:16]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][CH:20]=2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 122990761-Bromo-3-methoxy-5-nitrobenzeneHCID 59775033HCID 59775033, compound

Product 1

HCID 57962099HCID 57962099, compoundYield 60.7%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

1-Bromo-3-methoxy-5-nitrobenzene (0.50 g, 2.00 mmol), tert-butyl (3-vinylphenyl)carbamate (0.56 g, 2.15 mmol), tetra-N-butylammonium chloride (59.9 mg, 0.22 mmol), palladium acetate (48 mg, 0.22 mmol), and triethylamine (0.75 mL, 5.39 mmol) were stirred in N,N-dimethylformamide (5.7 mL) and heated to 110° C. for 20 hours. The mixture was cooled to RT, ethyl acetate and brine were added. The ethyl acetate was separated and the aqueous layer was extracted two more times with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica chromatography using ethyl acetate and hexanes gave the desired compound (0.45 g, 60%). LCMS for C20H23N2O5 (M+H)+: m/z=371.2.

Workup

  1. temperatureThe mixture was cooled to RT
  2. customThe ethyl acetate was separated
  3. extractionthe aqueous layer was extracted two more times with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica chromatography

Sources & evidence

ORD record
ord-176167d28a9f427ab3024a7cdfb253e2
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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