Boron tribromide → HCID 22396867, compound

HRID 1370459Notes

Reaction equation

HRID 1370459 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29]C)=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22396623HCID 22396623, compound

Product 1

HCID 22396867HCID 22396867, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of 3-benzoyl-10-(2-methoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (936 mg, 2.36 mmol) in CH2Cl2 (20 mL) was treated with BBr3 (0.75 mL, 7.94 mmol). The reaction was stirred at room temperature under nitrogen for 16.5 hours. The reaction was cooled to 0° C. and slowly quenched with saturated NH4Cl solution. After stirring at room temperature for 1.7 hours the reaction was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated in vacuo to give 792 mg (88%) of a yellow foam as the title compound: MS m/z 383.3 (M++H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customslowly quenched with saturated NH4Cl solution
  3. stirringAfter stirring at room temperature for 1.7 hours the reaction
  4. extractionwas extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-538cb4e3f43e4720a4e7eb38b5b238d7
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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