Tert-butyl cis-3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate → 2-(7-Ethylimidazo[1,2-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline

HRID 1095741Notes

Reaction equation

HRID 1095741 reaction equation
[F:1][C@H:2]1[C@@H:7]([O:8]S(C)(=O)=O)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[CH2:20]([C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[C:34](O)[CH:35]=[CH:36][CH:37]=4)[N:32]=3)=[CH:29][N:30]=[C:24]2[CH:23]=1)[CH3:21]>>[CH2:20]([C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[C:34]([O:8][C@@H:7]5[CH2:6][CH2:5][NH:4][CH2:3][C@H:2]5[F:1])[CH:35]=[CH:36][CH:37]=4)[N:32]=3)=[CH:29][N:30]=[C:24]2[CH:23]=1)[CH3:21]

Participants

3

Reactant 2

HCID 52324470Tert-butyl cis-3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylateHCID 667814032-(7-Ethylimidazo[1,2-a]pyridin-3-yl)quinolin-8-ol

Product 1

HCID 667821812-(7-Ethylimidazo[1,2-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline

Procedure

Prepared according to the procedure for Example 16, using (cis)-tert-butyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate in place of tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate and 2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinolin-8-ol in place of 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol. MS APCI (+) m/z 391.2 (M+1) detected.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-29709715ba3f48ce81fde52e9213e868
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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