Potassium Carbonate → HCID 10282458, compound

HRID 2229197Notes

Reaction equation

HRID 2229197 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][N:19]([CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[C:23]=2[Cl:32])=[O:21])[CH:7]=1.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42](B(O)O)[CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.ClCCl.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>[Cl:32][C:23]1[C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=1[C:20]([N:19]([CH2:18][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[C:9]=1[CH2:8][C:6]1[CH:7]=[C:2]([C:42]2[CH:41]=[N:40][CH:45]=[CH:44][CH:43]=2)[CH:3]=[CH:4][C:5]=1[O:38][CH3:39])[CH2:33][CH2:34][CH:35]([CH3:36])[CH3:37])=[O:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 10232691HCID 10232691, compound

Product 1

HCID 10282458HCID 10282458, compoundYield 89.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 61 mg (0.1 mmol) N-({3-[(5-bromo-2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 2 mL toluene is treated with 4 mg (0.003 mmol) tetrakis(triphenylphosphine)palladium(0), 15 mg (0.12 mmol) pyridine-3-boronic acid and 0.2 mL 2M potassium carbonate. The solution is heated to 85° C. for 18 hr and cooled to room temperature. The solution is diluted with 10 mL dichloromethane, washed with 10 mL brine, dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude residue. The residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford 55 mg (89%) (2-chloro-3,4-dimethoxyphenyl)-N-({3-[(2-methoxy-5-(3-pyridyl)phenyl)methyl](imidazol[1,2-a]pyridin-2-yl)}methyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 613.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with 10 mL brine
  3. dry with materialdried over anhydrous MgSO4
  4. customthe solvent removed in vacuo
  5. customto give the crude residue
  6. customThe residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH)

Sources & evidence

ORD record
ord-00ac713efafb44129bc80075896216be
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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