Dimethylformamide → N-(4-Fluoro-benzyl)-4-(3-pyrazin-2-yl-indole-1-sulfonyl)-benzamide

HRID 737045Notes

Reaction equation

HRID 737045 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)CCC.[F:20][C:21]1[CH:49]=[CH:48][C:24]([CH2:25][NH:26][C:27](=[O:47])[C:28]2[CH:33]=[CH:32][C:31]([S:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:39](I)=[CH:38]3)(=[O:36])=[O:35])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1.CN(C=O)C>O.CCOC(C)=O>[F:20][C:21]1[CH:49]=[CH:48][C:24]([CH2:25][NH:26][C:27](=[O:47])[C:28]2[CH:29]=[CH:30][C:31]([S:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:39]([C:6]4[CH:11]=[N:10][CH:9]=[CH:8][N:7]=4)=[CH:38]3)(=[O:36])=[O:35])=[CH:32][CH:33]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27373162-(Tributylstannyl)pyrazineHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

Product 1

HCID 58974984N-(4-Fluoro-benzyl)-4-(3-pyrazin-2-yl-indole-1-sulfonyl)-benzamide

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Degas DMF with N2 for 30 minutes. Add 2-tributylstannyl pyrazine (0.214 g, 0.58 mmol), N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide 0.300 g, 0.56 mmol) and tetrakis(triphenylphosphine)Pd(0) (0.100 g, 0.086 mmol) to DMF (5.0 ml). Heat and stir at 100° under N2 for 16 h. Pour the reaction mixture into H2O-EtOAc. Separate the EtOAc layer and extract several times with H2O, wash with brine, dry (MgSO4) and filter through celite. Remove the solvent on the rotary evaporator to give an oil. Chromatograph on the chromatron using a 1 mm plate and elute with 1% CH3OH—CH2Cl2 to give the title compound. Mass spectrum (m/e) (M+H) 487.1240; found: 487.1220.

Workup

  1. customDegas DMF with N2 for 30 minutes
  2. temperatureHeat
  3. customSeparate the EtOAc layer
  4. extractionextract several times with H2O
  5. washwash with brine
  6. dry with materialdry (MgSO4)
  7. filtrationfilter through celite
  8. customRemove the solvent
  9. customon the rotary evaporator
  10. customto give an oil
  11. washelute with 1% CH3OH—CH2Cl2

Sources & evidence

ORD record
ord-3c62c7848e8c4be386e1cd1b549313ec
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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