Boron tribromide → 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acid

HRID 1714060Notes

Reaction equation

HRID 1714060 reaction equation
B(Br)(Br)Br.[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:37]([O:39]C)=[O:38])=[CH:16][C:17]=3[N:18]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=4)[CH2:22][C:21]4[CH:33]=[CH:34][CH:35]=[CH:36][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C(Cl)Cl>[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:37]([OH:39])=[O:38])=[CH:16][C:17]=3[N:18]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=4)[CH2:22][C:21]4[CH:33]=[CH:34][CH:35]=[CH:36][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68506634methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

Product 1

HCID 1166995814-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acidYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (5 eq, 1 M sol. in CH2Cl2) was added to a solution of methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate in CH2Cl2 (0.06 M), and the mixture stirred at RT for 40 mins. The volatiles were removed in vacuo. The crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 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 in a 7% yield (over two steps).

Workup

  1. customThe volatiles were removed in vacuo
  2. customThe crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-12de96f2a82c4371a4fd0e77a496d500
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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