Methyl iodide → HCID 66570996, compound

HRID 1619281Notes

Reaction equation

[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25]>CN(C=O)C>[C:1]([N:5]([CH3:25])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 2.5 °C

Procedure

(74 mg, 266 μmol) 5-Phenylethynyl-pyridine-2-carboxylic acid tert-butylamide (Example 1, step 2) was dissolved in DMF (1 ml) and cooled to 0-5° C. NaH (55%) (14 mg, 319 μmol, 1.2 equiv.) was added and the mixture was stirred for 30 min at 0-5° C. Iodomethane (22 μl, 346 μmol, 1.3 equiv.) was added, and the mixture was then stirred for 1 hour at room temperature. The reaction mixture was evaporated and treated with sat. NaHCO3 solution and extracted twice with a small volume of CH2Cl2. The organic layers were loaded directly to silica gel column and the crude material was purified by flash chromatography on silica gel (20 g, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 5-phenylethynyl-pyridine-2-carboxylic acid tert-butyl-methyl-amide (48 mg, 62% yield) was obtained as a light yellow solid, MS: m/e=293.0 (M+H+).

Workup

stirringthe mixture was then stirred for 1 hour at room temperature
customThe reaction mixture was evaporated
additiontreated with sat. NaHCO3 solution
extractionextracted twice with a small volume of CH2Cl2
customthe crude material was purified by flash chromatography on silica gel (20 g, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record: ord-35869fab5ef844669bcb8273f48da3b9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772300B2

Reaction notes

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