Boron tribromide → HCID 11712662, compound

HRID 1714023Notes

Reaction equation

HRID 1714023 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([O:35]C)=[O:34])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=[O:27])[CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][C:17]4[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([OH:35])=[O:34])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=[O:27])[CH2:23][N:24]([CH3:25])[CH3:26])[CH2:18][C:17]4[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68501766HCID 68501766, compound

Product 1

HCID 11712662HCID 11712662, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 14-cyclohexyl-6-(N,N-dimethylglycyl)-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate from (Step 6) in DCM (0.15 M) was added dropwise to a solution of BBr3 in DCM (1 M, 5 eq.). The solution was stirred at RT for 1 h. Some drops of saturated aqueous NaHCO3 were added before volatiles were removed in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 μm, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (28%).

Workup

  1. customwere removed in vacuo
  2. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 μm, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-90c4de3ce65a47c59e15aefb16dc61f5
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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