Methyl iodide → (trans)-Naphthalen-2-ylmethyl 3-methoxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

HRID 1095709Notes

Reaction equation

HRID 1095709 reaction equation
[H-].[Na+].[OH:3][C@H:4]1[C@H:8]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([C:20]2[N:24]4[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:28][C:23]4=[N:22][CH:21]=2)[CH:16]=[CH:15]3)[CH2:7][N:6]([C:34]([O:36][CH2:37][C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[O:35])[CH2:5]1.I[CH3:49]>CN(C=O)C>[CH3:49][O:3][C@H:4]1[C@H:8]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([C:20]2[N:24]4[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:28][C:23]4=[N:22][CH:21]=2)[CH:16]=[CH:15]3)[CH2:7][N:6]([C:34]([O:36][CH2:37][C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)=[O:35])[CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131729511(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

Product 1

HCID 131729512(trans)-Naphthalen-2-ylmethyl 3-methoxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.017 g, 0.43 mmol) was added to a solution of (trans)-naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (0.117 g, 0.194 mmol) in DMF (1 mL). The reaction was cooled to 0° C. and stirred for 20 minutes. Iodomethane (0.012 ml, 0.194 mmol) was added, and the ice bath was removed. The reaction was stirred for 1 hour. Water was added, and the reaction mixture was extracted with CHCl3. The combined organic layers were washed with brine, dried and condensed. The residue was purified by silica gel chromatography to provide 54 mg of the desired product. MS APCI (+) m/z 619.1 (M+1) detected.

Workup

  1. customthe ice bath was removed
  2. stirringThe reaction was stirred for 1 hour
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with CHCl3
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. customcondensed
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a56d9e29e2584bbbb698c472b15c06cf
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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