Boron tribromide → HCID 57721189, compound

HRID 1394173Notes

Reaction equation

HRID 1394173 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=[C:10]2[C:18]2[C:19]([NH2:23])=[N:20][O:21][N:22]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[NH2:23][C:19]1[C:18]([C:10]2[N:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=2)=[N:22][O:21][N:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57721185HCID 57721185, compound

Product 1

HCID 57721189HCID 57721189, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Example 30 (100 mg, 0.32 mmol) in anhydrous dichloromethane (1.0 ml) stirred at 0° C., was added dropwise a 10M solution of boron tribromide (2.91 ml, 2.92 mmol) in dichloromethane and the mixture stirred at room temperature for 16 hours. The reaction was then quenched with water (20 ml), and the pH adjusted to 14 with 50% sodium hydroxide solution. The aqueous phase was washed with dichloromethane (×3), neutralised with 5N hydrochloric acid, and the resulting precipitate collected, washed with water (×3), diethyl ether and dried in vacuo to yield the title compound (59 mg, 62%); MS (ES+) m/e 295 [M+H]+.

Workup

  1. customThe reaction was then 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-5ac04a72ee0547b6802bfced0b6ff06e
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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