Sodium Carbonate → HCID 178420070, compound

HRID 2182351Notes

Reaction equation

HRID 2182351 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28]2[N:32](C(=O)C)[C:31]3[CH:36]=[CH:37][C:38](Br)=[CH:39][C:30]=3[N:29]=2)=[N:20]1)(=O)C>O1CCCC1.C(OCC)(=O)C>[C:7]1([C:37]2[CH:38]=[CH:39][C:30]3[N:29]=[C:28]([C:21]4[NH:20][N:19]=[C:27]5[C:22]=4[CH:23]=[CH:24][CH:25]=[CH:26]5)[NH:32][C:31]=3[CH:36]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22477978HCID 22477978, compound

Product 1

HCID 178420070HCID 178420070, compoundYield 122.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 mg of sodium carbonate, 7 mg of dihydrogendichlorobis(di-tert-butylphosphonite-κP)palladate(2-) (POPd[0]) and 46 mg of phenylboronic acid are added under an argon atmosphere to a solution of 50 mg of 1-[2-(1-acetyl-1H-indazol-3-yl)-5-bromobenzimidazol-1-yl]ethanone in 800 μl of anhydrous tetrahydrofuran. The reaction mixture is brought to reflux for 3 hours and then cooled to ambient temperature. The mixture is then diluted with 3 ml of ethyl acetate and then washed with 2 times 2 ml of water. The organic phase is dried over magnesium sulphate and then concentrated to dryness under reduced pressure. 48 mg of a brown solid are obtained, which solid is dissolved in 500 μl of tetrahydrofuran, to which 500 μl of diethylamine are added. The reaction mixture is heated at 60° C. for 4 hours and then allowed to return to ambient temperature. The mixture is then concentrated to dryness and then the brown solid obtained is purified by LC-MS to produce 12.5 mg of 3-(6-phenyl-1H-benzimidazol-2-yl)-2H-indazole (6); analytical retention time 3.10, MS 311 [M+H]+.

Workup

  1. temperatureto reflux for 3 hours
  2. washwashed with 2 times 2 ml of water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-093bf4a25ce14a739ad82e8d751aa946
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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