4-Toluenesulfonyl chloride → HCID 86646366, compound

HRID 1964912Notes

Reaction equation

HRID 1964912 reaction equation
[N+](C1C=C([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])C=CC=1)([O-])=O.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:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:18]2[CH:19]=[C:20]3[C:12]([CH:10]=[O:11])=[CH:13][N:14]([S:47]([C:44]4[CH:45]=[CH:46][C:41]([CH3:51])=[CH:42][CH:43]=4)(=[O:49])=[O:48])[C:15]3=[N:16][CH:17]=2)[CH:22]=1

Participants

7

Reactant 4

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

Product 1

HCID 86646366HCID 86646366, 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-dd0ad1a166934cc992c9e6ec9cd89cfb
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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