HCID 58959686, compound → HCID 58959693, compound

HRID 272567Notes

Reaction equation

HRID 272567 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:14]=1[F:23])=[CH:6][C:7]([O:9]CC)=O)[CH3:2]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:22][O:21][C:19]([C:17]1[C:18]2[C:7](=[O:9])[CH:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])[NH:12][C:13]=2[C:14]([F:23])=[CH:15][CH:16]=1)=[O:20]

Participants

3

Reactant 1

HCID 58959686HCID 58959686, compound

Product 1

HCID 58959693HCID 58959693, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
300 °C

Procedure

A suspension of 33 (25.0 g, 73.7 mmol) in Dowtherm A (200 mL) was heated to 300° C. over the course of 30 minutes and then stirred at 300° C. for 1 h. The reaction solution was cooled to room temperature and purified by flash chromatography (Hexanes to EtOAc) to afford a white solid (34, 12.1 g, 56.1%). 1H NMR (CDCl3, 300 MHz) δ 9.19 (br s, 1H), 7.42 (t, J=8.2, 1H), 7.21-7.25 (m, 1H), 6.92 (s, 1H), 4.51 (q, J=7.1, 2H), 3.99 (s, 3H), 1.46 (t, J=7.1, 3H).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. custompurified by flash chromatography (Hexanes to EtOAc)
  3. customto afford a white solid (34, 12.1 g, 56.1%)

Sources & evidence

ORD record
ord-3c1ea7e6d0434ab8960badac20e76bb0
Source dataset
uspto-grants-2008_11
Patent number
US07456178B2

Reaction notes

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