Potassium tert-butoxide → tert-butyl 2,4-di-tert-butoxy-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate

HRID 1481774Notes

Reaction equation

HRID 1481774 reaction equation
F[C:2]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[CH:19]=[CH:18]3)[C:12]([CH:25]=[CH2:26])=[C:11](F)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH3:28][C:29]([CH3:32])([O-:31])[CH3:30].[K+]>C1COCC1>[C:29]([O:31][C:2]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[CH:19]=[CH:18]3)[C:12]([CH:25]=[CH2:26])=[C:11]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])([CH3:32])([CH3:30])[CH3:28]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 89422971tert-butyl 2,4-difluoro-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate

Product 1

HCID 89422958tert-butyl 2,4-di-tert-butoxy-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinateYield 196.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of tert-butyl 2,4-difluoro-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate (72 mg, 0.2 mmol) in THF (1.0 mL) at −78° C. was added a solution of potassium tert-butoxide (1.0 M×0.48 mL, 0.48 mmol). The temperature was allowed to rise to room temperature and the reaction was quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate. The organic layers were combined, dried, evaporated and purified by silica chromatography (0-10% ethyl acetate in hexanes) to give tert-butyl 2,4-di-tert-butoxy-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate (94 mg, 47%).

Workup

  1. customto rise to room temperature
  2. customthe reaction was quenched with saturated NH4Cl
  3. extractionThe mixture was extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. custompurified by silica chromatography (0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e891cadbc2494f96984e14c8d797fb89
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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