Boron tribromide → HCID 178514713, compound

HRID 639390Notes

Reaction equation

HRID 639390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[O:30]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4[CH:21]=[C:22]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[OH:30]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178488251HCID 178488251, compound

Product 1

HCID 178514713HCID 178514713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-{4-[3-(4-Chloro-3-methoxy-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-benzenesulfonamide (Example 40) (94 mg, 0.2057 mmoles) is suspended in CH2Cl2 (20 mL) and cooled to −0° C. BBr3 (0.5 mL, 1M in CH2Cl2) is added dropwise at −0° C. After 10 min the suspension is warmed to rt and kept at that temperature overnight. The reaction is quenched with 1 mL of water and the reaction mixture is concentrated. The residue is chromatographed on SiO2 (3% methanol/CH2Cl2) affording the title compound: ES-MS 443.1 [M+H]; single peak at tR=4.318 min (System 3); Rf=0.53 (100% EtOAc).

Workup

  1. temperatureAfter 10 min the suspension is warmed to rt
  2. customkept at that temperature overnight
  3. customThe reaction is quenched with 1 mL of water
  4. concentrationthe reaction mixture is concentrated
  5. customThe residue is chromatographed on SiO2 (3% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-595d42944db943749d3a176cb48a3cbb
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

Loading…