Methanesulfonyl chloride → HCID 22571140, compound

HRID 1615204Notes

Reaction equation

HRID 1615204 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:13]([CH3:12])(=[O:15])=[O:14])[CH:3]=2)[NH:7]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27732135-Amino-2-oxindole

Product 1

HCID 22571140HCID 22571140, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5-aminoindolin-2-one (50 mg, 0.34 mmol) in DMF (1 mL) was added methanesulfonyl chloride (51 mg, 0.51 mmol) and DMAP (1 mg). The solution was stirred at rt for 16 h and the product was precipitated with ether, filtered and dried to give 10 mg, 13% of a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.22 (s, 1H), 7.13 (d, J=8.3 Hz, 1H), 6.87 (d, J=7.6 Hz, 1H), 3.55 (s, 2H), 2.91 (s, 3H).

Workup

  1. customthe product was precipitated with ether
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-5057973b3ef543a6892a2ed00db01c64
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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