Tetrabutylammonium Fluoride → Bpr-0L075

HRID 710324Notes

Reaction equation

HRID 710324 reaction equation
[Si]([C:8]1[N:9](C(=O)C)[C:10]2[C:15]([C:16]=1[C:17](=[O:30])[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1)=[CH:14][CH:13]=[C:12]([O:31][CH3:32])[CH:11]=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:32][O:31][C:12]1[CH:11]=[C:10]2[C:15]([C:16]([C:17]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[O:30])=[CH:8][NH:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667265851-(2-(tert-Butyldimethylsilyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)ethanone

Product 1

HCID 10359957Bpr-0L075Yield 108.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of the product of Step A (0.52 g, 1.05 mmol) and 1M TBAF in THF (1 ml) in THF (10 ml) was refluxed for 2 h. The solvent was evaporated and the residue was taken in EtOAc, washed with 1M HCl and organic layer was passed through silica gel bead. The solvent was evaporated and the residue was crystallized from MeOH to give the desired product (0.39 g; 100%), as creamy solid. 1H-NMR (CDCl3) 3.83 (s, 3H); 3.87 (s, 3H); 3.91 (s, 3H); 6.93-6.96 (m, 2H); 7.06 (s, 2H); 7.62 (s, 1H); 8.22 (d, 1H, J=9.36 Hz); 9.24 (broad s, 1H).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. washwashed with 1M HCl and organic layer
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-6433c02f67ba429f87cf496d8a538c65
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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