Water → HCID 23092434, compound

HRID 1896059Notes

Reaction equation

HRID 1896059 reaction equation
Cl.[CH3:2][C:3]1[C:8](C(O)=O)=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:6]=[C:5]([CH3:16])[N:4]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[OH2:41].[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:39]([NH:36][C:8]1[C:3]([CH3:2])=[N:4][C:5]([CH3:16])=[CH:6][C:7]=1[C:12]([F:13])([F:14])[F:15])=[O:41])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 671281022,6-Dimethyl-4-trifluoromethylpyridine-3-carboxylic acid hydrochloride

Product 1

HCID 23092434HCID 23092434, compoundYield 68%

Procedure

2,6-Dimethyl-4-trifluoromethylpyridine-3-carboxylic acid hydrochloride (23.17 g, 90.6 mmol) was suspended in tert-butanol (175 mL), and subsequent to the addition of Diphenylphosphorylazide (DPPA) (35.25 g, 128.1 mmol) and triethylamine (31.36 g, 309.9 mmol), the suspension was subjected to heating under reflux for 3 hours. Water (100 mL) was added to the reaction mixture, followed by extraction from chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (silica gel: 400 g; developer: hexane:acetone=10:1) to obtain the title compound (18.01 g, 68%) as a pale yellow oil.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. extractionfollowed by extraction from chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (silica gel: 400 g; developer: hexane:acetone=10:1)

Sources & evidence

ORD record
ord-1fdb611ffc264ace8c462afec3136286
Source dataset
uspto-grants-2013_08
Patent number
US08518936B2

Reaction notes

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