Boron tribromide → HCID 86723792, compound

HRID 577567Notes

Reaction equation

HRID 577567 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]([CH2:13][C:14]3[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])[CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[CH:4][C:3]=1[O:24]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]([CH2:13][C:14]3[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])[CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86723793HCID 86723793, compound

Product 1

HCID 86723792HCID 86723792, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 6-chloro-4-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-methoxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (124c, 500 mg, 1.38 mmol) in anhydrous DCM (10 mL) was added slowly a solution of BBr3 (1 M in DCM, 4.00 mL, 4.00 mmol). The reaction mixture was stirred at 0° C. for 3 hours, then quenched with water, and further diluted with water to 100 mL. The resulting mixture was extracted with DCM (3×100 mL). The combined organic phases were dried over sodium sulfate, and concentrated under vacuum to give 6-chloro-4-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (124d, 456 mg, 95% yield) as a solid.

Workup

  1. customquenched with water
  2. additionfurther diluted with water to 100 mL
  3. extractionThe resulting mixture was extracted with DCM (3×100 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-91d01fc38153462981516e0fc087cada
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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