Cesium carbonate → 5-(8-((trans)-3-Fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazole

HRID 1095700Notes

Reaction equation

HRID 1095700 reaction equation
N1(C([O-])=O)CCCCC1.[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][N:18]2[C:21]([C:24]3[CH:33]=[C:32]([C:34]4[O:38][CH:37]=[N:36][CH:35]=4)[C:31]4[C:26](=[C:27]([OH:39])[CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:22][N:23]=[C:17]2[CH:16]=1.[F:40][C@H:41]1[C@@H:46](OS(C)(=O)=O)[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42]1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[F:40][C@H:41]1[C@H:46]([O:39][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]3[C:26]=2[N:25]=[C:24]([C:21]2[N:18]4[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][O:11][CH3:10])=[CH:16][C:17]4=[N:23][CH:22]=2)[CH:33]=[C:32]3[C:34]2[O:38][CH:37]=[N:36][CH:35]=2)[CH2:45][CH2:44][NH:43][CH2:42]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 21874245Piperidine carboxylateHCID 52324470Tert-butyl cis-3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylateHCID 667813982-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-(oxazol-5-yl)quinolin-8-ol

Product 1

HCID 667821865-(8-((trans)-3-Fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazoleYield 3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
106 °C

Procedure

Preparation of (trans)tert-butyl 3-fluoro-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-oxazol-5-yl)quinolin-8-yloxy)piperidine-1-carboxylate: To 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-(oxazol-5-yl)quinolin-8-ol (9 mg, 0.02 mmol) in DMA (2 mL) was added (cis)-tert-butyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (13 mg, 0.04 mmol) and Cs2CO3 (22 mg, 0.07 mmol). The reaction vial was sealed and heated to 106° C. for 4 hours. The reaction was cooled to ambient temperature and concentrated. The crude residue was purified by flash column chromatography (DCM/MeOH 10:1) providing the desired product (3%).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. temperatureThe reaction was cooled to ambient temperature
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash column chromatography (DCM/MeOH 10:1)

Sources & evidence

ORD record
ord-b2c6029bbc1a406fb14ee99529b9b35b
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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