Methyl iodide → HCID 12994070, compound

HRID 1581758Notes

Reaction equation

[H-].[Na+].[CH3:3]I.[OH:5][C:6]([C:12]1[CH:25]=[CH:24][C:23]2[C:14](=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[CH:18][CH:17]=[N:16]3)[N:13]=1)([CH3:11])[C:7]([CH3:10])([CH3:9])[CH3:8]>>[CH3:3][O:5][C:6]([C:12]1[CH:25]=[CH:24][C:23]2[C:14](=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[CH:18][CH:17]=[N:16]3)[N:13]=1)([CH3:11])[C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 10085069HCID 10085069, compound

Product 1

HCID 12994070HCID 12994070, compoundYield 55.2%

Procedure

By employing General Procedure II, NaH (0.008 g, 0.3 mmol), methyl iodide (0.020 mL, 0.3 mmol), and the corresponding 1-hydroxy-1,2,2-trimethylpropyl phenanthroline (0.023 g, 0.08 mmol), prepared as described by Example 5, were reacted to provide 0.013 g (55% yield) of the title methyl ether as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.23 (dd, J=4.50, 1.80 Hz, Hp9), 8.23 (dd, J=7.80, 1.80 Hz, Hp7), 8.17 (d, J=8.70 Hz, Hp4), 7.88 (d, J=8.40 Hz, Hp3), 7.81 and 7.74 (two d, J=8.70 Hz, Hp5 and Hp6), 7.60 (dd, J=8.00, 4.40 Hz, Hp8), 3.21 (s, OCH3), 1.94 (s, CH3), 0.98 (s, (CH3)3); 13C NMR (75 MHz) δ163.79, 150.37, 145.12, 143.90, 135.97, 134.34, 128.82, 127.18, 126.47, 125.99, 122.53, 121.43, 86.16, 51.36, 38.83, 26.10, 17.78; IR (CHCl3) 2957 (C—H Ar), 2928 (CH), 857 (C—H Ar) cm−1; HRMS m/e Calcd for C19H23N2O (MH+): 295.1810, found, 295.1818.

Workup

customwere reacted

Sources & evidence

ORD record: ord-d84cee2181f64151bff8d9c6fdac9e88
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730788B1

Reaction notes

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