Tetrabutylammonium Fluoride → HCID 71284985, compound

HRID 1481739Notes

Reaction equation

HRID 1481739 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH3:44])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]1[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])[C:24](=[O:37])[C:23]([C:38]([O:40][CH3:41])=[O:39])=[CH:22][C:21]=1[CH2:42][CH3:43])=[CH:15][CH:14]=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:36][O:35][C:28]1[CH:29]=[C:30]([O:33][CH3:34])[CH:31]=[CH:32][C:27]=1[CH2:26][N:25]1[C:20]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH3:44])[C:11]([CH2:10][CH2:9][OH:8])=[CH:19]3)=[C:21]([CH2:42][CH3:43])[CH:22]=[C:23]([C:38]([O:40][CH3:41])=[O:39])[C:24]1=[O:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71284147HCID 71284147, compound

Product 1

HCID 71284985HCID 71284985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of methyl 6-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (6.10 g, 9.84 mmol) in THF (60 mL) was added TBAF solution (1M THF, 15.0 mL, 15.0 mmol). Reaction mixture was stirred at room temperature for 30 min until starting material was completely consumed. THF was then concentrated and residue was purified by column chromatography (EtOAc/DCM, 0-100% gradient). Methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(2-(2-hydroxyethyl)-1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate was obtained as yellow solid (4.56 g, 92%).

Workup

  1. customReaction mixture
  2. customwas completely consumed
  3. concentrationTHF was then concentrated
  4. customresidue was purified by column chromatography (EtOAc/DCM, 0-100% gradient)

Sources & evidence

ORD record
ord-1a9be20828d040b0aa58d096eebb4135
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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