Boron tribromide → 1-(3-amino-1H-indazol-5-yl)-3-(3-hydroxybenzyl)urea

HRID 222381Notes

Reaction equation

HRID 222381 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=3)=[O:13])[CH:9]=2)[NH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)=[O:13])[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 236585511-(3-amino-1H-indazol-5-yl)-3-(3-methoxybenzyl)urea

Product 1

HCID 250098491-(3-amino-1H-indazol-5-yl)-3-(3-hydroxybenzyl)ureaYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of 1-(3-amino-1H-indazol-5-yl)-3-(3-methoxybenzyl)urea are suspended in 10 ml of DCM, and 916 μl of BBr3 are added. After two days at RT, the mixture is carefully quenched using 1 ml of methanol and evaporated to dryness. Purification by silica-gel chromatography (eluent: DCM/MeOH 4:1) gives 400 mg of 1-(3-amino-1H-indazol-5-yl)-3-(3-hydroxybenzyl)urea (“A2) as a virtually colourless solid (84%); MS-FAB (M+H+)=298.

Workup

  1. customthe mixture is carefully quenched
  2. customevaporated to dryness
  3. customPurification by silica-gel chromatography (eluent: DCM/MeOH 4:1)

Sources & evidence

ORD record
ord-09d13331937e4998bd6d44b2e7a636f1
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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