Pyrrolidine → (S)-N-allyl-6-(6-cyclopropyl-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide
Reaction equation
[CH2:1]([N:4]([C@@H:33]([CH3:38])[C:34]([F:37])([F:36])[F:35])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15](C(OC(C)(C)C)=O)[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([CH:23]2[CH2:25][CH2:24]2)[CH:17]=3)=[N:12][CH:13]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].N1CCCC1>C(#N)C>[CH2:1]([N:4]([C@@H:33]([CH3:38])[C:34]([F:35])([F:37])[F:36])[S:5]([C:8]1[CH:13]=[N:12][C:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([CH:23]2[CH2:25][CH2:24]2)[CH:17]=3)=[CH:10][CH:9]=1)(=[O:6])=[O:7])[CH:2]=[CH2:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-tert-butyl 2-(5-(N-allyl-N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-6-cyclopropyl-1H-indole-1-carboxylate (500 mg, 0.91 mmol) in acetonitrile was added pyrrolidine (0.35 mL, 4.55 mmol). The mixture was stirred at room temperature for 5 hrs and the solvent was evaporated. The residue was purified on silica gel eluting with 0 to 10% ethyl acetate in CH2Cl2 to provide (S)-N-allyl-6-(6-cyclopropyl-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (370 mg, 91% yield). MS m/z 450.2 M+H+; 1H NMR (500 MHz, CDCl3): δ 9.28 (1H, s), 8.85 (1H, s), 7.96 (1H, d, J=5.5 Hz), 7.74 (1H, d, J=9.5 Hz), 7.49 (1H, d, J=5.5 Hz), 7.09 (1H, s), 7.01 (1H, s), 6.82-6.80 (1H, m), 5.75 (1H, m), 5.16-5.10 (2H, m), 4.64-4.62 (1H, m), 3.89 (2H, d, J=5.0 Hz), 2.00-1.96 (1H, m), 1.35 (3H, d, J=6.0 Hz), 0.98-0.96 (2H, m), 0.75-0.72 (2H, m).
Workup
- customthe solvent was evaporated
- customThe residue was purified on silica gel eluting with 0 to 10% ethyl acetate in CH2Cl2
Sources & evidence
- ORD record
- ord-abc321093f284c2d9e8878c3bdd2346e
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735414B2
Reaction notes
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