HCID 67496496, compound → HCID 86664836, compound

HRID 1628299Notes

Reaction equation

HRID 1628299 reaction equation
[F:1][C:2]([F:21])([C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[C:8]([N+:18]([O-:20])=[O:19])[CH:7]=1)[C:3]([OH:5])=[O:4]>C1(C)C=CC=CC=1>[F:21][C:2]([F:1])([C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[C:8]([N+:18]([O-:20])=[O:19])[CH:7]=1)[C:3]([O:5][C:6]([CH3:11])([CH3:7])[CH3:2])=[O:4]

Participants

3

Reactant 1

HCID 67496496HCID 67496496, compound

Product 1

HCID 86664836HCID 86664836, compoundYield 176.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-difluoro-2-(3-nitro-5-(pyridin-4-yl)phenyl)acetic acid 52.D (450 mg, 1.53 mmol) in toluene (5 mL) was added n,n-dimethylformamide di-tert-butyl acetal (1.47 mL, 6.12 mmol). The mixture was stirred at 50° C. for 1 hour, then concentrated and dried under vacuum. The residue was then dissolved in EtOAc (10 mL), to which was added 10% Pd/C (150 mg). The air was then evacuated out of the flask and replaced by hydrogen. The mixture was stirred at room temperature for 2 hours, filtered over celite and then concentrated to afford tert-butyl 2-(3-amino-5-(pyridin-4-yl)phenyl)-2,2-difluoroacetate 52.E (473 mg, 96% yield) which is used in the next step with no further purification.

Workup

  1. concentrationconcentrated
  2. customdried under vacuum
  3. dissolutionThe residue was then dissolved in EtOAc (10 mL), to which
  4. additionwas added 10% Pd/C (150 mg)
  5. customThe air was then evacuated out of the flask
  6. stirringThe mixture was stirred at room temperature for 2 hours
  7. filtrationfiltered over celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-374cf22f1f5e43ef94e8f4a14cb17283
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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