Potassium Carbonate → HCID 11433816, compound

HRID 2099796Notes

Reaction equation

HRID 2099796 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH:21]([C:36]3[NH:37][CH:38]=[CH:39][N:40]=3)[CH2:22][C:23]3[CH:31]=[C:30]([CH3:32])[C:29]4[C:25](=[CH:26][N:27]([CH2:33][O:34][CH3:35])[N:28]=4)[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[F:41][C:42]1[CH:43]=[C:44]([CH:47]=[C:48]([F:50])[CH:49]=1)[CH2:45]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@@H:21]([C:36]3[N:37]([CH2:45][C:44]4[CH:43]=[C:42]([F:41])[CH:49]=[C:48]([F:50])[CH:47]=4)[CH:38]=[CH:39][N:40]=3)[CH2:22][C:23]3[CH:31]=[C:30]([CH3:32])[C:29]4[C:25](=[CH:26][N:27]([CH2:33][O:34][CH3:35])[N:28]=4)[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5188963,5-Difluorobenzyl bromideHCID 69071669HCID 69071669, compound

Product 1

HCID 11433816HCID 11433816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1H-Imidazol-2-yl)-2-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (102 mg, 0.19 mmol), 3,5-difluorobenzyl bromide (27.0 μL, 0.21 mmol, 1.1 equiv), and potassium carbonate (54 mg, 3.0 equiv) were combined in dimethylformamide (2.0 mL). After stirring at room temperature for 16 h, the reaction mixture was removed in vacuo and the residue purified by column chromatography to afford 72.0 mg (57%). Mass spec.: 667.4 (MH)+.

Workup

  1. customthe reaction mixture was removed in vacuo
  2. customthe residue purified by column chromatography
  3. customto afford 72.0 mg (57%)

Sources & evidence

ORD record
ord-bd1c68d21b0149b699bd0953cb179019
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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