Boron tribromide → HCID 59681770, compound

HRID 1394199Notes

Reaction equation

HRID 1394199 reaction equation
[Br:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[C:9]([C:19]3[C:20]([NH2:24])=[N:21][O:22][N:23]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.B(Br)(Br)Br>ClCCl>[NH2:24][C:20]1[C:19]([C:9]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:3]3[C:2]([Br:1])=[CH:7][N:6]=[CH:5][C:4]=3[N:8]=2)=[N:23][O:22][N:21]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59681797HCID 59681797, compound

Product 1

HCID 59681770HCID 59681770, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 187 (0.1 g, 0.26 mmol) in anhydrous dichloromethane (10 ml) stirred at 0° C., was added dropwise boron tribromide (1.0 M solution in dichloromethane, 2.3 ml, 2.3 mmol) and the mixture stirred at room temperature for 16 hours. The reaction was quenched with water (20 ml), basified to pH 14 with 50% sodium hydroxide solution. The aqueous phase was washed with dichloromethane 3×, neutralised with 6 N hydrochloric acid, and the resulting precipitate collected, washed with water 3×, diethyl ether and dried in vacuo to yield the title product (40 mg, 40%); MS (ES+) m/e 374 [M+H]+.

Workup

  1. customThe reaction was quenched with water (20 ml)
  2. washThe aqueous phase was washed with dichloromethane 3×
  3. customthe resulting precipitate collected
  4. washwashed with water 3×, diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-43f961291c244a2eb2b9cbeee5c64533
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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