Pyridine → HCID 178483343, compound

HRID 2240094Notes

Reaction equation

HRID 2240094 reaction equation
CC1C=CC(S(OCCC2C=CC=C3C=2NN=C3S(C2C=CC=CC=2)(=O)=O)(=O)=O)=CC=1.[C:32]1([S:38]([C:41]2[C:49]3[C:44](=[C:45]([CH2:50][CH2:51]O)[CH:46]=[CH:47][CH:48]=3)[NH:43][N:42]=2)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N:53]1[CH:58]=CC=C[CH:54]=1.C1(C)C(S([Cl:68])(=O)=O)=CC=CC=1>ClCCl>[ClH:68].[CH3:54][N:53]([CH3:58])[CH2:51][CH2:50][C:45]1[CH:46]=[CH:47][CH:48]=[C:49]2[C:44]=1[NH:43][N:42]=[C:41]2[S:38]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 178427713HCID 178427713, compoundHCID 178527302HCID 178527302, compound

Product 1

HCID 178483343HCID 178483343, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[3-(Phenylsulfonyl)-1H-indazol-7-yl]ethyl 4-methylbenzenesulfonate To a solution of 2-[3-(phenylsulfonyl)-1H-indazol-7-yl]ethanol (0.64 g, 2.12 mmol) in anhydrous dichloromethane (30 mL) at 0° C. was added pyridine (0.43 mL) and toluenesulfonyl chloride (0.475 g, 2.5 mmol). The solution was stirred for 12 hours at room temperature. The mixture was concentrated in vacuo and taken up in ethyl acetate (30 mL). The organic layer was washed with 2 M HCl, (2×25 mL), brine, dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (50% ethyl acetate/petroleum ether) gave the title compound as a white foam (0.9 g, 93%). Mp: 61-64° C. MS (ES−): 455 (M−H) Step 7

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washThe organic layer was washed with 2 M HCl, (2×25 mL), brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1793ee27c5d74e0fa7bf7c03f81c95e7
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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