Dimethylformamide → HCID 135830952, compound

HRID 1824789Notes

Reaction equation

HRID 1824789 reaction equation
Cl[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[C:17](I)=[CH:16][C:15]([OH:19])=[CH:14][C:12]=2[N:13]=1.[C:20]([Cu])#[N:21].[CH3:23][N:24](C=O)C>C(OCC)(=O)C>[C:23]([C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[C:17]([C:20]#[N:21])=[CH:16][C:15]([OH:19])=[CH:14][C:12]=2[N:13]=1)#[N:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 135830956HCID 135830956, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 135830952HCID 135830952, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To 2-(2-chloro-4-hydroxy-phenyl)-7-iodo-benzooxazol-5-ol (279 mg) in DMF (5 mL) was added CuCN (97 mg). The mixture was placed in an oil bath and heated to 150° C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl acetate and washed with 1N HCl, saturated aqueous EDTA, brine (3×), dried (Na2SO4), and concentrated. Material was purified by preparative LC/MS. MS: 278 (MH+), HPLC tR: 1.92 min. The HPLC conditions used are the following: HPLC Waters Corp. Novapak HR™ C 18 RCM 40×100 mm 6 μm particle; flow rate 40 mL/min, linear gradient from 35% B to 65% B over 15 min; A=water, 0.1% TFA; B=MeOH, UV detection at 254 nm and positive ionization mass spectrometry detection

Workup

  1. customThe mixture was placed in an oil bath
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with 1N HCl, saturated aqueous EDTA, brine (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customMaterial was purified by preparative LC/MS

Sources & evidence

ORD record
ord-6cd4f5521fab416c9cbe0eb2edb80d22
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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