Toluene → HCID 89968832, compound

HRID 2206902Notes

Reaction equation

HRID 2206902 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C:13]2([C:27]([F:30])([F:29])[F:28])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[C:22]([Br:24])[C:21]([CH2:25]O)=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(C)C=CC=CC=1.C1(P([N:54]=[N+:55]=[N-:56])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O.C1COCC1>[N:54]([CH2:25][C:21]1[C:22]([Br:24])=[N:23][C:18]([N:15]2[CH2:16][CH2:17][C:13]([C:5]3[CH:4]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=3)([C:27]([F:30])([F:29])[F:28])[CH2:14]2)=[CH:19][CH:20]=1)=[N+:55]=[N-:56]

Participants

7

Reactant 4

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 87159219HCID 87159219, compound

Product 1

HCID 89968832HCID 89968832, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-bromopyridin-3-yl)methanol (1.55 g), toluene (10 ml) and THF (5 ml), which had been stirred under ice cooling, diphenylphosphoryl azide (1.59 g) and subsequently 1,8-diazabicyclo[5.4.0]-7-undecene (0.88 g) were added, and then stirred overnight at room temperature. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off and the residue was purified by silica gel chromatography to obtain 3-(azidomethyl)-6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-bromopyridine (1.35 g).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd609ad0aa33494c9575152e6b6aba31
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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