Water → HCID 18518659, compound

HRID 1369128Notes

Reaction equation

HRID 1369128 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[C:11]([Br:17])[CH:12]=[C:13]([I:16])[CH:14]=2)[C:9]([OH:28])([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[C:8]1=[O:29].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].O>ClCCl>[CH3:37][S:38]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[C:11]([Br:17])[CH:12]=[C:13]([I:16])[CH:14]=2)[C:9]([OH:28])([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[C:8]1=[O:29])(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18518591HCID 18518591, compound

Product 1

HCID 18518659HCID 18518659, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-hydroxypentyl)-4-bromo-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole (155 mg, 0.279 mmol) and triethylamine (0.06 mL, 0.43 mmol) in dichloromethane (5 mL) was added methanesulfonyl chloride (0.025 mL, 0.323 mmol) at 0° C. The mixture was stirred for 5 min at the same temperature and water was added. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 3:2 hexane/ethyl acetate to give the mixture (116 mg) of the title compound and dimesylate.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 3:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-d53d2683136045b29d7901781d2be409
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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