Sodium hydride → HCID 178516757, compound

HRID 1452458Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:14][CH2:13][C:12](=[O:15])[NH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][N:20]=1.[Al]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:14][CH2:13][C:12](=[O:15])[N:11]([CH2:25][C:22]3[CH:21]=[N:20][C:19]([Cl:18])=[CH:24][CH:23]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 25 °C

Procedure

DMF was stirred for 10 min while being degassed with dry N2. 3-(3-bromo-4-fluorophenyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one (200 mg 0.74 mmol) was then added and the mixture was degassed an additional 5 min. NaH (21 mg. 0.88 mmol) was added and the solution turned yellow; the solution was purged continuously with N2, then 2-chloro-5-chloromethypyridine (143 mg. 0.88 mmol) was added. The flask was covered with aluminum foil and stirred at approximately 25° C. for approximately 48 hours. TLC indicated a mixture of the desired product and three other components. The reaction mixture was poured into 20 mL water and 30 mL EtOAc, extracted 2× with EtOAc and the combined organics were washed with brine, dried over MgSO4, filtered and evaporated. The crude residue was purified via flash column (50% EtOAc/Hex) and evaporation of the product fractions gave ˜165 mg of material which (by NMR) appeared to be a mixture of the materials shown below.

Workup

customwhile being degassed with dry N2
customthe mixture was degassed an additional 5 min
customthe solution was purged continuously with N2

Sources & evidence

ORD record: ord-2887b50ca67145abbfc81a9878bd070e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473669B2

Reaction notes

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