Boron tribromide → HCID 22091465, compound

HRID 2229194Notes

Reaction equation

HRID 2229194 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25]C)=[C:6]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][NH:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:7]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][NH:19][CH2:20][CH2:21][CH:22]([CH3:23])[CH3:24])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22091521HCID 22091521, compound

Product 1

HCID 22091465HCID 22091465, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 416 mg (1.0 mmol) of ({3-[(5-bromo-2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl) (3-methylbutyl)amine in 20 mL dichloromethane at −78° C. is treated with boron tribromide 0.4 mL (4.0 mmol). The resulting solution is allowed to return to room temperature over 1 hr, quenched by addition of 10 mL sat. NaHCO3 and extracted with 2×10 mL dichloromethane. The combined extract is dried over anhydrous MgSO4 and the solvent removed in vacuo to yield 360 mg (89%) ({3-[(5-bromo-2-hydroxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(3-methylbutyl)amine.

Workup

  1. customquenched by addition of 10 mL sat. NaHCO3
  2. extractionextracted with 2×10 mL dichloromethane
  3. extractionThe combined extract
  4. dry with materialis dried over anhydrous MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4ddc0bd7a9e94425aee687c24fd39d3c
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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