2-Methoxyethanol → 2-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

HRID 1159933Notes

Reaction equation

HRID 1159933 reaction equation
ClC1C=C(NC2N=C(C3C(C4C=C(NC(=O)C5C(F)=CC=CC=5F)C=CC=4)=NN4C=CC=CC=34)C=CN=2)C=CC=1OCCN(C)C.[CH3:47][O:48][CH2:49][CH2:50][OH:51].[H-].[Na+].[F:54][C:55]1[CH:56]=[C:57]([N+:62]([O-:64])=[O:63])[CH:58]=[CH:59][C:60]=1F>>[F:54][C:55]1[CH:56]=[C:57]([N+:62]([O-:64])=[O:63])[CH:58]=[CH:59][C:60]=1[O:51][CH2:50][CH2:49][O:48][CH3:47]

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 11505567N-[3-(3-{2-[(3-Chloro-4-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

Product 1

HCID 234980752-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

Procedure

In a procedure analogous to Example 125, 0.64 g of the title compound was prepared from 0.39 mL (4.94 mmol) of 2-methoxyethanol, 0.24 g (6.11 mmol) of a 60% mineral oil dispersion of sodium hydride, and 0.75 g (4.7 mmol) of 3,4-difluoronitrobenzene as a light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 3.44 (s, 3H), 3.80 (d, 2H, J=4.6 Hz), 4.28 (t, 2H, J=4.6 Hz), 7.05 (dd, 1H, J=8.4 and 8.4 Hz), 7.98 (dd, 1H, J=10.6 and 2.7 Hz), and 8.03 (d, 1H, J=9.0 Hz).

Sources & evidence

ORD record
ord-df06fbd9d5df41e2886216c396d687ba
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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