Sodium Iodide → 6-Butyl-8-[(1-{4-[(1,1-di methylethyl)sulfonyl]butyl}-4-piperidinyl)oxy]quinoline, formate salt

HRID 1363023Notes

Reaction equation

[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[I-].[Na+].[C:24](=O)([OH:26])[O-:25].[Na+].[CH3:29][C:30]([S:33]([CH2:36][CH2:37][CH2:38][CH2:39]Br)(=[O:35])=[O:34])([CH3:32])[CH3:31]>CN(C=O)C.CO>[CH:24]([OH:26])=[O:25].[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:17][CH2:18][N:19]([CH2:39][CH2:38][CH2:37][CH2:36][S:33]([C:30]([CH3:29])([CH3:32])[CH3:31])(=[O:34])=[O:35])[CH2:20][CH2:21]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (65 mg, 0.23 mmol), sodium iodide (47 mg, 0.3 mmol), sodium bicarbonate (190 mg, 2.2 mmol) and 4-bromobutyl 1,1-dimethylethyl sulfone (for example, as prepared for Intermediate 22) (94 mg) in DMF (2 ml) was heated in a Smith Creator™ microwave oven at 150° C. for 20 min. The reaction mixture was applied to an SCX-2 cartridge (10 g), preconditioned with methanol, and eluted with methanol, followed by 10% aqueous 0.88 s.g. ammonia in methanol. The ammoniacal fractions were combined and concentrated in vacuo and the residue (100 mg) was purified by MDAP to give the title compound (58 mg, 46%): LCMS RT=2.65 min, ES+ve m/z 461 (M+H)+.

Workup

washeluted with methanol
customfollowed by 10% aqueous 0.88 s
concentrationconcentrated in vacuo
customthe residue (100 mg) was purified by MDAP

Sources & evidence

ORD record: ord-9154c77da73e436da2b2b34738348fc5
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884114B2

Reaction notes

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