Phthalimide → HCID 21935949, compound

HRID 1242477Notes

Reaction equation

HRID 1242477 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:3]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:1][C:2]1[C:7]([CH2:8][N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Product 1

HCID 21935949HCID 21935949, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.25 g (0.94 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (example 1M]), 0.15 g (1.03 mmol) of phthalimide and 0.32 g (1.20 mmol) of triphenylphosphine were dissolved in 10 ml of THF. The stirred reaction mixture was cooled down to 0° C. and a solution of 0.27 g (1.15 mmol) of di-tert.-butyl azodicarboxylate in 2 ml of THF was added drop by drop. Then, the reaction was warmed up to ambient temperature. After 1 hour, the solvent was evaporated and the residue purified by crystallization from MeCl2 and n-heptane to give 0.32 g of the title compound as a colorless solid.

Workup

  1. customThe stirred reaction mixture
  2. temperatureThen, the reaction was warmed up to ambient temperature
  3. customthe solvent was evaporated
  4. customthe residue purified by crystallization from MeCl2 and n-heptane

Sources & evidence

ORD record
ord-159a54ba921345c188ba4aefde87eaf7
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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