Cesium carbonate → HCID 86704970, compound

HRID 572160Notes

Reaction equation

HRID 572160 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([O:13][C:14]3[NH:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:27]1[N:28]([CH2:36][CH3:37])[N:29]=[C:30]2[CH:35]=[CH:34][CH:33]=[N:32][C:31]=12.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC.O>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>[NH:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:27]2[N:28]([CH2:36][CH3:37])[N:29]=[C:30]3[CH:35]=[CH:34][CH:33]=[N:32][C:31]=23)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 18180031Water 1,2-dimethoxyethaneHCID 866889652-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazoleHCID 86704969HCID 86704969, compound

Product 1

HCID 86704970HCID 86704970, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazole (116 mg), 3-bromo-2-ethyl-2H-pyrazolo[4,3-b]pyridine (71 mg), tetrakis(triphenylphosphine)palladium(0) (36.3 mg), cesium carbonate (153 mg) and DME/water (3/1, 4 ml) was subjected to microwave irradiation at 120° C. for 40 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate/hexane to give the title compound (66.0 mg).

Workup

  1. customirradiation at 120° C. for 40 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-98999a0f41604d079cc61d343ce295f3
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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