4-Toluenesulfonyl chloride → HCID 58086639, compound

HRID 250609Notes

Reaction equation

HRID 250609 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([N-]C(C)C)(C)C.[Li+].C1CCCCC1.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>O1CCCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[N:14]([S:47]([C:44]3[CH:45]=[CH:46][C:41]([CH3:51])=[CH:42][CH:43]=3)(=[O:49])=[O:48])[CH:13]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8078CyclohexaneHCID 2724682Lithium diisopropylamideHCID 58086168HCID 58086168, compound

Product 1

HCID 58086639HCID 58086639, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To (3-nitro-phenyl)-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (536, 291 mg, 0.85 mmol) in tetrahydrofuran (7 mL) was added 1.5 M of lithium diisopropylamide in cyclohexane (676 μl , 1.59 mmol) at −78° C. under an atmosphere of nitrogen. After 30 minutes, p-toluenesulfonyl chloride (209 mg, 1.10 mmol) was added in tetrahydrofuran and the reaction was stirred for three hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. All solids were filtered and purified by silica gel column chromatography eluting with 60% ethyl acetate in hexane to give the compound (537, 182 mg, 43%). MS (ESI) [M+H+]+=499.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationAll solids were filtered
  6. custompurified by silica gel column chromatography
  7. washeluting with 60% ethyl acetate in hexane
  8. customto give the compound (537, 182 mg, 43%)

Sources & evidence

ORD record
ord-db1caddd00dc47d7be49f818d87a5eff
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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