Boron tribromide → HCID 178424876, compound

HRID 1024418Notes

Reaction equation

HRID 1024418 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11]C)[NH:7][N:6]=[C:5]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[NH:7][N:6]=[C:5]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178486922HCID 178486922, compound

Product 1

HCID 178424876HCID 178424876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.3 1.24 g of “4b” are dissolved in 12 ml of dichloromethane under argon and cooled to 0° C. 3.45 ml of boron tribromide are added dropwise, and the mixture is stirred at room temperature for a further 16 hours. The mixture is subjected to conventional work-up, and the residue is, for further purification, chromatographed over a 120 g RP18 silica-gel column, giving 578 mg of 5-bromo-6-hydroxy-3-(3-methylbenzyl)-1H-indazole (“4c”).

Workup

  1. customthe residue is, for further purification
  2. customchromatographed over a 120 g RP18 silica-gel column

Sources & evidence

ORD record
ord-c482b2a4c1074af099b12094f32ebbe8
Source dataset
uspto-grants-2014_05
Patent number
US08722903B2

Reaction notes

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