Sodium hydride → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-2-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 448579

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

14a (100 mg) was dissolved in DMF with 5-methanesulfonyl-2,3-dihydro-1H-indole (0.3 mmol) and NaH (0.3 mmol). The mixture was heated at 90° C. for 4 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and water. The organic layer was washed with a saturated NaHCO3 solution, isolated, evaporated and purified by preparative HPLC to give 14-1, LCMS 475.1 (MH+).

Workup

temperatureAfter cooling to room temperature
washThe organic layer was washed with a saturated NaHCO3 solution
customisolated
customevaporated
custompurified by preparative HPLC
customto give 14-1, LCMS 475.1 (MH+)

Sources & evidence

ORD record: ord-2c15132c73784c47bc92e879453f3492
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481731B2

Linked notes

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