Sodium bis(trimethylsilyl)amide → HCID 86643798, compound

HRID 1802470Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2Cl.N[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:22]#[N:23].[CH3:28][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[C:8](=[C:7]([NH:6][C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:22]#[N:23])[CH:28]=[C:5]3[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:4]3=2)[CH:9]=[CH:10][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridine (Example 1, Step 5) (250 mg, 0.94 mmol) and 3-amino-4-methylbenzonitrile (136mg, 1.03 mmol) in THF (9.3 mL) at 0° C. was added NaHMDS (1.8 mL, 1 M in THF, 1.80 mmol). The reaction stirred at 0° C. for 15 minutes and then quenched by the addition of sat. aq. NaHCO3 solution. The precipitated solid was collected by filtration, washed with EtOAc and dried under vacuum.

Workup

customquenched by the addition of sat. aq. NaHCO3 solution
filtrationThe precipitated solid was collected by filtration
washwashed with EtOAc
customdried under vacuum

Sources & evidence

ORD record: ord-2f9be8d4ffc44af4b97e31db5a3748c5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

Loading…