Water → 4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenol

HRID 341289Notes

Reaction equation

HRID 341289 reaction equation
[Cl:1][C:2]1[CH:31]=[N:30][C:5]2[N:6]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)=[CH:9][CH:8]=3.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[N:30][C:5]2[N:6]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 461864403-chloro-6-(4-methoxyphenyl)-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indole

Product 1

HCID 461829684-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenolYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-6-(4-methoxyphenyl)-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indole (222 mg, 1.11 mmol, 1eq.) in CH2Cl2 at 0° C., BBr3 (4.46 ml, 1M in CH2Cl2 4.46 mmol) was added dropwise. After 3 h at room temperature, the reaction mixture is hydrolysed with H2O and extracted with AcOEt (3×50 ml), dried with MgSO4, then filtered. The solvents were removed under reduced pressure and the crude material was purified by flash chromatography (CH2Cl2 then AcOEt) to afford 4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenol (409 mg, 0.94 mmol, 85% yield. 1H NMR 1H ((CD3)2CO, 300 MHz), δ 8.67 (d, 1H, J=2.3 Hz), 8.45-8.51 (m, 4H), 8.16-8.20 (m, 2H), 7.93 (dd, 1H, J=2.1 Hz, 8.9 Hz), 7.54-7.68 (m, 5H), 6.98 (d, 2H, J=8.6 Hz).

Workup

  1. extractionextracted with AcOEt (3×50 ml)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customThe solvents were removed under reduced pressure
  5. customthe crude material was purified by flash chromatography (CH2Cl2

Sources & evidence

ORD record
ord-94a518d5a6424ea991850f8f579a28b0
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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