Sodium Carbonate → HCID 18437414, compound

HRID 1643216Notes

Reaction equation

HRID 1643216 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:29][C:30]3[CH:38]=[CH:37][C:33]4[O:34][CH2:35][O:36][C:32]=4[CH:31]=3)[CH2:12][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][CH3:28])[C:15](I)=[N:16][C:17]=3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1B(O)O>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=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>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:29][C:30]3[CH:38]=[CH:37][C:33]4[O:34][CH2:35][O:36][C:32]=4[CH:31]=3)[CH2:12][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][CH3:28])[C:15]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=4[CH3:45])=[N:16][C:17]=3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 10054673HCID 10054673, compound

Product 1

HCID 18437414HCID 18437414, compoundYield 73.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of bis-benzo[1,3]dioxol-5-ylmethyl-(3-butyl-2-iodo-5-phenyl-3H-imidazol-4-ylmethyl)-amine (62 mg, 0.1 mmol) and Pd(PPh3)4 (6 mg) in 1 ml of toluene is added aqueous sodium carbonate (0.4 ml of 2.0 N) and 2-methylphenyl boronic acid (18 mg, 0.13 mmol, 1.3 eq.) in 0.3 ml of ethanol under nitrogen, the resulting mixture is stirred at 100° C. for 8 h. After being cooled to room temperature, the reaction mixture is diluted with 10 ml of ethyl acetate, washed with water and brine and dried over sodium sulfate. Concentration and purification by flash chromatography affords 43 mg of bis-benzo[1,3]dioxol-5-ylmethyl(3-butyl-5-phenyl-2-o-tolyl-3H-imidazol-4-ylmethyl)-amine 1H NMR (400 MHz, CDCl3) δ 7.70 (2H, d, J=7.2 Hz), 7.43˜7.24 (7H, m), 6.77˜6.67 (6H, m), 5.94 (4H, s) 3.87 (2H, t, J=7.6 Hz), 3.78 (2H, s), 3.37 (4H, s), 2.20 (3H,s), 1.17 (2H, m), 0.88 (2H, m), 0.63 (3H, t, J=7.2 Hz); MS (+VE) m/z 588 (M+1).

Workup

  1. temperatureAfter being cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration and purification by flash chromatography

Sources & evidence

ORD record
ord-dc629d66177b4b6d81009b62ab43e714
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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