Tetrabutylammonium Fluoride → Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate

HRID 1481711Notes

Reaction equation

HRID 1481711 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[S:16][C:17]([C:19]3[C:28]([CH2:29][CH3:30])=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([O:31][CH3:32])[N:20]=3)=[CH:18][C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:29]([C:28]1[C:19]([C:17]2[S:16][C:13]3[N:14]([CH3:15])[C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[CH:18]=2)=[N:20][C:21]([O:31][CH3:32])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])[CH3:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71281709Methyl 6-(5-((tert-butyldimethylsilyloxy)methyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-5-ethyl-2-methoxynicotinate

Product 1

HCID 71281796Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinateYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of methyl 6-(5-((tert-butyldimethylsilyloxy)methyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-5-ethyl-2-methoxynicotinate (0.594 g, 1.25 mmol) in THF (8 mL) was added solution of TBAF (1M THF, 1.50 mL, 1.50 mmol). Reaction mixture was stirred at room temperature for 30 min and THF was then concentrated. Residue was loaded directly on the column and product was isolated eluting with EtOAc/hexanes gradient (0-50%). Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (0.233 g, 26% 2 steps) was obtained as solid.

Workup

  1. customReaction mixture
  2. concentrationTHF was then concentrated
  3. customproduct was isolated
  4. washeluting with EtOAc/hexanes gradient (0-50%)

Sources & evidence

ORD record
ord-060719690091471ab5641fc461a53176
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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