Cesium carbonate → N-[6-(Methoxymethyl)-2-pyridinyl]-2,2-dimethylpropanamide

HRID 1255398Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][CH3:10])[N:3]=1.[C:11]([NH-:17])(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:10][O:9][CH2:8][C:4]1[N:3]=[C:2]([NH:17][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-bromo-6-methoxymethylpyridine [1.00 g; J Heterocyclic Chem., 30, 563, (1993)], pivaloyl amide (0.756 g), palladium acetate (0.112 g), cesium carbonate (2.40 g), 4.5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.434 g) and 1,4-dioxan (5 ml) were sealed in a microwave vial and heated in a microwave oven with stirring for 30 minutes at 150° C. This process was repeated with a second batch of reagents and the products combined, the insoluble material filtered from solution and the filtrate evaporated under reduced pressure. The residue was purified by chromatography (silica; hexane/ethyl acetate) to afford the desired product as a yellow oil, 1.75 g. 1H NMR (CDCl3) δ: 9.84 (1H, s), 7.82 (1H, d), 6.87 (1H, d), 4.43 (2H, s), 3.48 (3H, s).

Workup

customwere sealed in a microwave vial
temperatureheated in a microwave oven
filtrationthe insoluble material filtered from solution
customthe filtrate evaporated under reduced pressure
customThe residue was purified by chromatography (silica; hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9cb3176d2ed6432ca1007a7d7e999f68
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461083B2

Reaction notes

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