Dichloromethane → HCID 178424071, compound

HRID 1353753Notes

Reaction equation

HRID 1353753 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[CH:14][N:13](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:12]=3)[CH:9]=2)[N:4](C2CCCCO2)[N:3]=1.[CH3:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[N:15]=[CH:14][NH:13][N:12]=4)[CH:9]=3)[NH:4][N:3]=2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 22479811HCID 22479811, compound

Product 1

HCID 178424071HCID 178424071, compoundYield 185.9%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-{3-bromo-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazolyl}perhydro-2H-pyran (0.150 g, 0.254 mmol), in ethylene glycol dimethyl ether (3 mL) was added 4-methylphenyl boronic acid (0.052 g, 0.381 mmol), [1,1′-bis(diphenylphosphino)-ferrocene] complex with dichloromethane (1:1) (0.030 g, 0.0254 mmol) and potassium phosphate (0.269 g, 1.27 mmol). The reaction mixture was heated to reflux temperature for 5 hours. The solvent was then evaporated to dryness and the residue was dissolved in 20 mL of ethyl acetate. The heterogeneous solution was washed 3 times with 10 mL of water and once with 10 mL of brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The resulting brown solid was adsorbed on silica gel and purified by column chromatography (85:15 hexanes/ethyl acetate) to provide the title compound (0.130 g, 85% yield): ES-MS (m/z) 602 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 5 hours
  3. customThe solvent was then evaporated to dryness
  4. dissolutionthe residue was dissolved in 20 mL of ethyl acetate
  5. washThe heterogeneous solution was washed 3 times with 10 mL of water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated to dryness
  8. custompurified by column chromatography (85:15 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-efad0ace1294457ea86ed781d138e75e
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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