Sodium Bicarbonate → HCID 58913532, compound

HRID 1296937Notes

Reaction equation

HRID 1296937 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28](I)=[CH:27][N:26]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28]([C:13]2[CH:12]=[CH:11][C:10]([CH2:24][NH2:25])=[CH:9][CH:14]=2)=[CH:27][N:26]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58913548HCID 58913548, compound

Product 1

HCID 58913532HCID 58913532, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 3-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (0.1 g, 0.15 mmol) in DMF (3 ml) was added 4-aminomethylboronic acid (0.028 g, 0.30 mmol). 1M sodium bicarbonate solution (0.5 ml, 0.5 mmol) was then added, followed by dichlorobis(triphenylphosphine) palladium 11 (0.011 g, 0.015 mmol). The mixture was degassed and then heated to 150° C., for 600 seconds under microwave irradiation. The mixture was then concentrated in vacuo and purified by column chromatography using dichloromethane and methanol as eluent to give 4-[3-(2,4-bis-benzyloxy-5-chloro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-benzylamine (0.025 g, 26%).

Workup

  1. customThe mixture was degassed
  2. concentrationThe mixture was then concentrated in vacuo
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-6420768dba784b24a9f22b2fbd2fa824
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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