Potassium Hydroxide → HCID 59487255, compound

HRID 1091905Notes

Reaction equation

HRID 1091905 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][CH:14]=[CH:15][C:8]=12)(C)C.[F:16][C:17]1[C:22]([CH:23]=[O:24])=[C:21]([F:25])[CH:20]=[CH:19][C:18]=1[NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28].[OH-].[K+].[Cl-].[NH4+]>O.CO>[C:6]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][CH:14]=[C:15]([CH:23]([OH:24])[C:22]3[C:17]([F:16])=[C:18]([NH:26][S:27]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)(=[O:29])=[O:28])[CH:19]=[CH:20][C:21]=3[F:25])[C:8]=12)#[CH:5]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 242292724-[(Trimethylsilyl)ethynyl]-1H-pyrrolo[2,3-b]pyridineHCID 58086928HCID 58086928, compound

Product 1

HCID 59487255HCID 59487255, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a round bottom flask 4-trimethylsilanylethynyl-1H-pyrrolo[2,3-b]pyridine (7, 0.250 g, 1.17 mmol), N-(2,4-difluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (4, 0.498 g, 1.36 mmol), and 2.0 mL of methanol were added and the suspension was stirred for 10 minutes. Potassium hydroxide (0.213 g, 3.79 mmol) was added and the reaction was stirred at room temperature for 6 hours. The reaction was poured into 25 mL of water and 25 mL of saturated ammonium chloride, then extracted with 50 mL or ethyl acetate. The organic layer was isolated and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluting with a gradient of 5 to 60% ethyl acetate in hexanes. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (8, 0.146 g).

Workup

  1. stirringthe reaction was stirred at room temperature for 6 hours
  2. extractionextracted with 50 mL or ethyl acetate
  3. customThe organic layer was isolated
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a gradient of 5 to 60% ethyl acetate in hexanes
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-c312ce6d43f54ced94ec9ea3d5f3815e
Source dataset
uspto-grants-2012_03
Patent number
US08129404B2

Reaction notes

Loading…