Triacetoxyperiodinane → 5-Cyclopropyl-N-methyl-2-(5-methylpyridin-2-yl)-6-[(methylsulfonyl)(2-oxoethyl)amino]-2H-indazole-3-carboxamide

HRID 1626955Notes

Reaction equation

HRID 1626955 reaction equation
[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][OH:20])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([C:4]2[C:12]([N:13]([S:14]([CH3:17])(=[O:15])=[O:16])[CH2:18][CH:19]=[O:20])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71766520HCID 71766520, compound

Product 1

HCID 866989535-Cyclopropyl-N-methyl-2-(5-methylpyridin-2-yl)-6-[(methylsulfonyl)(2-oxoethyl)amino]-2H-indazole-3-carboxamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Compound (2) (278 mg) in DCM (6 mL) was added Dess-Martin periodinane (400 mg, 0.94 mmol). The mixture was stirred at room temperature for 1 h and then diluted with DCM (10 mL) and washed with aq. saturated NaHCO3 solution (10 mL) and water (10 mL). The organic phase was filtered to remove insoluble impurities, dried (MgSO4) and concentrated in vacuo to afford (i) (276 mg) which was used in the next step without further purification. ESI-MS m/z calculated for [M+MeOH]+: 474.2. found: 474.2.

Workup

  1. washwashed with aq. saturated NaHCO3 solution (10 mL) and water (10 mL)
  2. filtrationThe organic phase was filtered
  3. customto remove insoluble impurities
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c36feb6701bd4486ba40603a723b7afa
Source dataset
uspto-grants-2014_07
Patent number
US08785478B2

Reaction notes

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