Ethyl orthoformate → HCID 59375009, compound

HRID 2361444Notes

Reaction equation

HRID 2361444 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[Br:12][C:13]1[C:14]([CH3:20])=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].[CH2:21](OC(OCC)OCC)C>C1COCC1.CCOC(C)=O>[Br:12][C:13]1[C:14]([CH3:20])=[C:15]([N:16]2[C:4](=[O:6])[C:3]3[C:2](=[CH:10][CH:9]=[C:8]([F:11])[CH:7]=3)[N:1]=[CH:21]2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 1014122-Amino-5-fluorobenzoic acidHCID 1235383-Bromo-o-toluidine

Product 1

HCID 59375009HCID 59375009, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-5-fluorobenzoic acid (1.00 g, 6.45 mmol), 3-bromo-2-methylaniline (1.199 g, 6.45 mmol) and triethoxymethane (0.955 g, 6.45 mmol) in THF (2 mL) was heated at 110° C. overnight in a sealed tube. The mixture was cooled to room temperature and diluted with EtOAc. The solution was washed with NaHCO3 (aq) and water, then was dried and concentrated. The residue was purified by column chromatography, eluting with EtOAc-hexane (gradient from 20:80 to 30:70) to provide the desired product as a white solid (1.2 g, 56% yield). LCMS (M+H)+ m/z 333, 335.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe solution was washed with NaHCO3 (aq) and water
  3. customwas dried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with EtOAc-hexane (gradient from 20:80 to 30:70)

Sources & evidence

ORD record
ord-8b5ffa58572e48069823bb9ea538cc96
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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