Ethanol → 4-(4-(4-Chlorophenyl)-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1685169Notes

Reaction equation

HRID 1685169 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH:16]=[C:17](Br)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH:16]=[C:17]([C:29]3[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 672650004-(4-Bromo-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 672647474-(4-(4-Chlorophenyl)-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Add 4-[4-bromo-1-(2-dimethylamino-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.0 g; 0.0024 mol; 1.0 equiv), 4-chloro phenyl boronic acid (0.58 g; 0.0037 mol; 1.5 equiv), 3M Na2CO3 solution (0.79 g; 0.0074 mol; 3.0 equiv) to ethanol (5 mL) and toluene (5 mL) and degas the reaction with argon. Add Pd(PPh3)4 (0.29 g; 0.00024 mol; 0.1 equiv) and microwave at 110° C. for 20 min. Add EA and filter through a Celite® bed. Add saturated NaHCO3 aqueous and extract with EA. Evaporate the organic layer, and purify the residue over a silica gel column with methanol in DCM to give the title compound (0.8 g; crude).

Workup

  1. customdegas
  2. customthe reaction with argon
  3. filtrationAdd EA and filter through a Celite® bed
  4. extractionAdd saturated NaHCO3 aqueous and extract with EA
  5. customEvaporate the organic layer
  6. custompurify the residue over a silica gel column with methanol in DCM

Sources & evidence

ORD record
ord-a73b2e17151147c2a0de242bee8385f5
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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