Methanol → HCID 178506184, compound

HRID 1994020Notes

Reaction equation

HRID 1994020 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.CO>CN(C=O)C>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[NH:11][C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=4)=[N:14][N:13]=3)=[CH:16][CH:17]=2)[CH:32]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 178515914HCID 178515914, compound

Product 1

HCID 178506184HCID 178506184, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-{[3-(trifluromethyl)phenyl]amino}-4H-1,2,4-triazol-3-yl)phenol (100 mg, 0.31 mmol) was dissolved in 2 mL of anhydrous DMF in 2-5 mL microwave vial (Personal Chemistry). Solid Cs2CO3 (203.4 mg, 0.62 mmol) was added, followed by 3-bromopyridine (74.0 mg, 0.468 mmol). The vial was capped and microwaved at 250° C. for 30 min. Then ca. 1 mL of MeOH was added to dissolve the formed suspension. The resulting reddish-brown solution was filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetontrile/water system with 0.01% of TFA. The fractions, containing the product, were collected and partitioned between EtOAc and saturated aqueous NaHCO3. Ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title compound as a yellow solid (22.4 mg).

Workup

  1. customThe vial was capped
  2. custommicrowaved at 250° C. for 30 min
  3. dissolutionto dissolve the formed suspension
  4. filtrationThe resulting reddish-brown solution was filtered through 0.22 u syringe
  5. filtrationfilter
  6. custompurified by reverse phase preparative HPLC
  7. additionThe fractions, containing the product
  8. customwere collected
  9. custompartitioned between EtOAc and saturated aqueous NaHCO3
  10. washEthyl acetate layer was washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-1a8c91b033d64389adc50b18c17bde3d
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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