Potassium Carbonate → tert-butyl 2,4-di-tert-butoxy-5-chloro-6-(1-methyl-1H-indol-5-yl)nicotinate

HRID 1481779Notes

Reaction equation

[C:1]([O:5][C:6]1[N:18]=[C:17](I)[C:16]([Cl:20])=[C:15]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][C:32](B(O)O)=[CH:33][CH:34]=2)[CH:29]=[CH:28]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]1[N:18]=[C:17]([C:32]2[CH:31]=[C:30]3[C:35](=[CH:34][CH:33]=2)[N:27]([CH3:26])[CH:28]=[CH:29]3)[C:16]([Cl:20])=[C:15]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 2,4-di-tert-butoxy-5-chloro-6-iodonicotinate (103 mg, 0.2 mmol), 1-methyl-1H-indol-5-ylboronic acid (53 mg, 0.3 mmol), PdCl2dppf (16 mg, 0.02 mmol), aqueous K2CO3 (2.0 M×0.4 mL, 0.8 mmol) in acetonitrile (1.0 mL) was stirred at 80° C. for 3 h and then extracted with ethyl acetate. The organic layers were combined and dried over sodium sulfate, evaporated and purified by silica chromatography (0-5% ethyl acetate in hexanes) to give tert-butyl 2,4-di-tert-butoxy-5-chloro-6-(1-methyl-1H-indol-5-yl)nicotinate (103 mg, 100%).

Workup

extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
customevaporated
custompurified by silica chromatography (0-5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-fde0c0be3a9946f6ae2f48813cb83540
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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