5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-methylbenzenamine → HCID 59436067, compound

HRID 1802469Notes

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.[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:34])=[C:31]([CH:33]=1)N)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[CH3:35]C(C)([O-])C.[Na+]>C1COCC1>[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:34])=[C:31]([NH:6][C:7]2[C:8]3[CH:9]=[CH:10][N:11]=[C:2]([Cl:1])[C:3]=3[C:4]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=3[CH:35]=2)[CH:33]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridine (Example 1, Step 5) (150 mg, 0.56 mmol) and 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylaniline (155 mg, 0.62 mmol) in THF (9.3 mL) was added sodium tert-butoxide (65 mg, 0.67 mmol). The reaction stirred at 60° C. for 30 minutes was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-50% EtOAc/heptane) afforded the title compound.

Workup

customwas then quenched by the addition of sat. aq. NaHCO3 solution
extractionThe mixture was extracted with EtOAc
washthe extracts were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification by silica gel column chromatography (0-50% EtOAc/heptane)

Sources & evidence

ORD record: ord-b23caacde74f49f59fbb2e43ba47f9e0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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