Sodium hydride → HCID 24888026, compound

HRID 2074106Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[NH:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25]Br>CN(C=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[N:11]([CH2:25][CH2:24][O:23][CH3:22])[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]pyridine (0.122 g, 0.48 mmol) in DMF (3 ml) was added NaH (19 mg, 0.48 mmol) and the suspension was stirred for 20 minutes under nitrogen. Methoxyethylbromide (45 μL, 0.48 mmol) was then added and the reaction mixture was heated to 100° C. under nitrogen for 18 hours. The solvent was removed in vacuo and the residue was purified by radial chromatography (2 mm plate, eluting with EtOAc) to give the title compound as a clear oil (90 mg, 60%). 1H NMR (400 MHz, DICHLOROMETHANE-D2) δ ppm 8.54 (d, 2 H), 7.61 (d, 2 H), 7.18-7.24 (m, 2 H), 7.03 (t, 2 H), 6.32 (s, 1 H), 4.19 (t, 2 H), 4.05 (s, 2 H), 3.72 (t, 2 H), 3.28 (s, 3 H); m/z (APCI+) for C18H18N3FO 312.0 (M+H)+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by radial chromatography (2 mm plate, eluting with EtOAc)

Sources & evidence

ORD record: ord-952bafa8d32d4a139520b32d3d38d283
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919488B2

Reaction notes

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