Boron tribromide → HCID 68502543, compound

HRID 1714048Notes

Reaction equation

HRID 1714048 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29]C)=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([OH:29])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68507183HCID 68507183, compound

Product 1

HCID 68502543HCID 68502543, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (prepared as described in Example 18, Step 5) in DCM (0.01 M) was added dropwise 5 eq of a solution of BBr3 in DCM (1 M). The solution was stirred at RT for 30 min. Volatiles were removed in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 μm, 30×100 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 (20%); MS (ES+) m/z 393 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 μm, 30×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-36aadd2dd70b4bd085eeec31016e2b3a
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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