Tetrabutylammonium Fluoride → HCID 118159441, compound

HRID 628404Notes

Reaction equation

HRID 628404 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:39]([CH3:42])=[N:40][N:41]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([CH2:20][O:21][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:14]=3)[C:6]=2[CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Br:1][C:2]1[C:3]2[N:4]([C:39]([CH3:42])=[N:40][N:41]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=[C:17]([Cl:19])[CH:18]=3)[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123928710HCID 123928710, compound

Product 1

HCID 118159441HCID 118159441, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-Bromo-6-[3-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-chlorobenzyl]-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (2.1 g, 3.2 mmol, from Step 3) in THF (30 mL) was treated with 1.0 M TBAF in THF (6.4 mL, 6.4 mmol, Aldrich) for 1 hour. The reaction mixture was diluted with water and extracted with three portions of EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% MeOH. Yield: (0.722 g, 54% over the two steps).

Workup

  1. extractionextracted with three portions of EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography
  7. washeluting with a gradient from 0-10% MeOH

Sources & evidence

ORD record
ord-41a7ed4681e34319b1d8aece8c5c5804
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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