Dimethylformamide → 7-(4-Methanesulfonyl-phenyl)-5-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1261904Notes

Reaction equation

HRID 1261904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[C:23]1(B(O)O)C=CC=CC=1.CB1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=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>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:4]2[N:5]3[C:10]([CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]3)=[C:2]([CH3:23])[CH:3]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 574072TrimethylboroxineHCID 667117075-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 2

HCID 667114737-(4-Methanesulfonyl-phenyl)-5-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazineYield 65%HCID 667117075-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
130 °C

Procedure

Into a 30 mL vial, 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.480 g, 0.00120 mol) (Note: 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine was prepared in an analogous fashion as Example 99b replacing Phenylboronic acid with $-methylsulfonuphenylboronic acid), Trimethylboroxine (1.37 g, 0.0109 mol), Tetrakis(triphenylphosphine)palladium (0) (0.14 g, 0.00012 mol) and Potassium carbonate (7.49 g, 0.0542 mol) were added and purged under an atmosphere of Nitrogen for 10 minutes. N,N-Dimethylformamide (25.0 mL, 0.323 mol) was then added and heated at 130° C. for 4 hours. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and MeOH as eluant (0 to 5% MeOH). The collected fractions afforded 7-(4-Methanesulfonyl-phenyl)-5-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.26 g, 65%).

Workup

  1. additionwere added
  2. custompurged under an atmosphere of Nitrogen for 10 minutes
  3. customThe reaction was partitioned with water and EtOAc
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solid was filtered
  8. washwashed with EtOAc
  9. customThe solvent was removed under vacuum
  10. customThe product was isolated via ISCO column chromatography with DCM and MeOH as eluant (0 to 5% MeOH)

Sources & evidence

ORD record
ord-f0adcd715bf64ffe9c07394549a1f97f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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