Methyl p-toluenesulfonate → 4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-(2-(7-methoxy-5-azaspiro[2.4]heptan-5-yl)ethoxy)quinoline

HRID 1510106Notes

Reaction equation

[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][C:32](=[O:34])[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2.[H-].[Na+].S(OC)([C:41]1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]4[CH2:33][CH:32]([O:34][CH3:41])[C:29]5([CH2:31][CH2:30]5)[CH2:28]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:35])[NH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

The above product from Example 2 (60 mg) was dissolved into DMF (4 ml) and cooled at 0° C. NaH (1.1 eq) was added to the reaction and stirred for 10 minutes. To the reaction was added TsOMe (1.2 eq), the solution was heated at 80° C. for two hours. The reaction was quenched with water and extracted with EtOAc followed by washing with water, then brine and dried over Na2SO4. The solution was evaporated and purified by silica column to give the titled product. Mass: (M+1), 492

Workup

temperaturethe solution was heated at 80° C. for two hours
customThe reaction was quenched with water
extractionextracted with EtOAc
washby washing with water
dry with materialbrine and dried over Na2SO4
customThe solution was evaporated
custompurified by silica column

Sources & evidence

ORD record: ord-2b72a516ef43496f9c11291fd33ad755
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211911B2

Reaction notes

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