Boron tribromide → 1-(3-amino-7-fluoro-6-hydroxy-1H-indazol-5-yl)-3-(3-fluorobenzyl)urea

HRID 222385Notes

Reaction equation

HRID 222385 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([F:26])[C:7]([O:23]CC)=[C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[O:13])[CH:9]=2)[NH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([F:26])[C:7]([OH:23])=[C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[O:13])[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 250100441-(3-amino-6-ethoxy-7-fluoro-1H-indazol-5-yl)-3-(3-fluorobenzyl)urea

Product 1

HCID 1358696081-(3-amino-7-fluoro-6-hydroxy-1H-indazol-5-yl)-3-(3-fluorobenzyl)ureaYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 mg of 1-(3-amino-6-ethoxy-7-fluoro-1H-indazol-5-yl)-3-(3-fluorobenzyl)urea are suspended in 2 ml of dichloromethane, and 105 μl of BBr3 are added. After 24 hours at RT, the mixture is carefully quenched using 1 ml of methanol and evaporated to dryness. Purification by chromatography on RP-18 silica gel (eluent:acetonitrile/water) gives 15 mg of 1-(3-amino-7-fluoro-6-hydroxy-1H-indazol-5-yl)-3-(3-fluorobenzyl)urea (“A 15”) as a virtually colourless solid (22%), MS-FAB (M+H+)=334;

Workup

  1. customthe mixture is carefully quenched
  2. customevaporated to dryness
  3. customPurification by chromatography on RP-18 silica gel (eluent:acetonitrile/water)

Sources & evidence

ORD record
ord-fe14e08c29794c91abac028d8f8b4774
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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