Boron tribromide → HCID 178519363, compound

HRID 2272034Notes

Reaction equation

HRID 2272034 reaction equation
B(Br)(Br)Br.[NH:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([N:16]3[C@@H:25]4[C@@H:20]([C:21]5[CH:29]=[CH:28][CH:27]=[C:26]([O:30]C)[C:22]=5[CH2:23][CH2:24]4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:13][C:8]=2[N:7]=[CH:6]1.C([O-])(O)=O.[Na+]>ClCCl>[NH:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([N:16]3[C@@H:25]4[C@@H:20]([C:21]5[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[C:22]=5[CH2:23][CH2:24]4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:13][C:8]=2[N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178488316HCID 178488316, compound

Product 1

HCID 178519363HCID 178519363, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 mol/L in dichloromethane, 0.5 mL) is added to a solution of (1H-benzoimidazol-5-yl)-(cis-7-methoxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl)-methanone (60 mg) in dichloromethane (5 mL) at room temperature. The resulting solution is stirred at room temperature for 2 h. Aqueous half-saturated NaHCO3 solution is added and the resulting neutral mixture is extracted with dichloromethane and dichloromethane/methanol (95:5). The combined extracts are washed with brine and dried (Na2SO4). The solvent is evaporated and the residue is triturated with diethyl ether and dried to give the title compound as a colorless solid. Yield: 30 mg (52% of theory); TLC: rf=0.45 (silica gel, CH2Cl2/MeOH/32% aqueous NH3 90:10:1); Mass spectrum (ESI+): m/z=348 [M+H]+.

Workup

  1. extractionthe resulting neutral mixture is extracted with dichloromethane and dichloromethane/methanol (95:5)
  2. washThe combined extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is evaporated
  5. customthe residue is triturated with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-18574e2201cd4c16bfec4d82b7783975
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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