Sodium Carbonate → 1-Isopropylsulfonyl-2-amino-6-(3-(methyl)-1-(phenyl)-pyrazol-5-yl)-benzimidazole

HRID 2252083Notes

Reaction equation

HRID 2252083 reaction equation
Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH:14]([S:17]([N:20]1[C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[NH2:32])(=[O:19])=[O:18])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH:14]([S:17]([N:20]1[C:24]2[CH:25]=[C:26]([C:2]3[N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:5]=[C:4]([CH3:13])[CH:3]=3)[CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[NH2:32])(=[O:18])=[O:19])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 179816815-Bromo-3-methyl-1-phenylpyrazoleHCID 17981723HCID 17981723, compound

Product 1

HCID 179818131-Isopropylsulfonyl-2-amino-6-(3-(methyl)-1-(phenyl)-pyrazol-5-yl)-benzimidazoleYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(bromo)-3-(methyl)-1-(phenyl)-pyrazole (264 mg, 1.11 mmol) in 6 mL DME add 1-isopropylsulfonyl-2-amino-benzimidazole-6-boronic acid (694 mg, 2.45 mmol). Add sodium carbonate (354 mg, 3.34 mmol) dissolved in 0.5 mL of water and trans-dichlorobis(triphenylphosphine) palladium (II) (234 mg, 0.33 mmol). Heat the mixture to 100° C. with stirring under nitrogen. After 2 hours, cool and filter over a pad of Celite® and sodium sulfate. Purify the crude product by radial chromatography eluting with 4% methanol in CH2Cl2 to yield 201 mg (46%) of the title compound. MS(ES+): m/z=396.0 (M+H)+

Workup

  1. temperaturecool
  2. filtrationfilter over a pad of Celite® and sodium sulfate
  3. customPurify the crude product by radial chromatography
  4. washeluting with 4% methanol in CH2Cl2

Sources & evidence

ORD record
ord-febd29c0667440aa920bf3f34a3e01da
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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