Methanol → HCID 57566615, compound

HRID 1929600Notes

Reaction equation

HRID 1929600 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[N+:35]([O-])([OH:37])=[O:36].CO>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:35]([O-:37])=[O:36])[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 944Nitric AcidHCID 9845Trifluoroacetic anhydrideHCID 57566613HCID 57566613, compound

Product 1

HCID 57566615HCID 57566615, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of N-[4-bromo-2-(3-fluoro-pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide (6.45 grams, 18.4 mmoles) in TFA (100 mL) and TFAA (25.5 mL, 183.6 mmole), at 0° C., was added a TFA solution (30 mL) of 90% fuming nitric acid (2.46 mL, 55.1 mmoles) over a 45 minute period. The mixture was then stirred at 0° C. for a total of 4 hours. The crude reaction (now homogenous) was poured into ice producing a pasty mass. The mixture was diluted to 500 mL total volume with water, treated with 50 mL of methanol, and vigorously stirred for 12 hours. The resulting solids were filtered, washed with copious amounts of water, then dried in vacuo at 50° C. to afford the title compound (6.1 grams, 82% yield) as a tan powder.

Workup

  1. customThe crude reaction (now homogenous)
  2. additionwas poured into ice producing a pasty mass
  3. stirringvigorously stirred for 12 hours
  4. filtrationThe resulting solids were filtered
  5. washwashed with copious amounts of water
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-5cc9c0905d7b45a0b0dbb1496a9b4493
Source dataset
uspto-grants-2012_05
Patent number
US08188095B2

Reaction notes

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