HCID 10429739, compound → HCID 22285782, compound

HRID 1061867Notes

Reaction equation

HRID 1061867 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(Cl)Cl>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 1

HCID 10429739HCID 10429739, compound

Product 1

HCID 22285782HCID 22285782, compoundYield 62.31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

300 mg (0.79 m mol) of 2-(4-aminosulfonylphenyl)-3-(4-methoxyphenyl)indole prepared in Example 70 was suspended in 20 ml of CH2Cl2 cooled in an ice-salt bath and the cold solution of 0.41 ml (4.4 m mol) of BBR3 in 5 ml of CH2Cl2 was added in dropwise. When addition was complete, the ice-salt bath was removed and the reaction mixture was stirred at room temperature for 3 h. The solvent was removed and the residue was purified by column chromtography eluting with 3:1 petroleum: ethyl acetate to give 180 mg of title compound as light yellow crystal, yield 62.31%, m.p. 241-243° C. The data of Nuclear Magnetic Resonance shown that: 1HNMR (300 MHz, DMSO)δ:6.80-7.77 (m, 11H, Ar—H), 9.43 (s, 1H, OH), 11.56 (s, 1H, N—H); Anal. Calcd for: C20H16N2O3S: C 56.92, H 4.43, N 7.69; Found: C 56.81, H 4.34, N 7.47.

Workup

  1. temperaturecooled in an ice-salt bath
  2. additionWhen addition
  3. customthe ice-salt bath was removed
  4. customThe solvent was removed
  5. customthe residue was purified by column chromtography
  6. washeluting with 3:1 petroleum

Sources & evidence

ORD record
ord-2b4327acf4464abd8bd4905067a644c7
Source dataset
uspto-grants-2005_11
Patent number
US06960611B2

Reaction notes

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