Trimethyl borate → 8,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

HRID 1472510Notes

Reaction equation

HRID 1472510 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[N:6]3[C:19]4[C:18]([C:4]=2[CH:3]=1)=[CH:17][CH:16]=[CH:15][C:14]=4[C:13]([CH3:21])([CH3:20])[C:12]1[C:7]3=[CH:8][CH:9]=[N:10][CH:11]=1.C([Li])CCC.[B:29](OC)([O:32]C)[O:30]C>C1COCC1.C1CCCCC1>[CH3:20][C:13]1([CH3:21])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][CH:11]=2)[N:6]2[C:19]3[C:18]([C:4]4[CH:3]=[C:2]([B:29]([OH:32])[OH:30])[CH:23]=[CH:22][C:5]=42)=[CH:17][CH:16]=[CH:15][C:14]1=3

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 672021773-bromo-8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthryleneHCID 178418339Butyllithium

Product 1

HCID 672019818,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

94 g (259 mmol) of 3-bromo-8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene are dissolved in 1500 ml of dry THF, 135 ml (337 mmol) of a 2.5 M solution of n-butyllithium in cyclohexane are added dropwise at −70° C., after 1 h 37 ml of trimethyl borate (336 mmol) are added dropwise, the mixture is warmed to room temperature over the course of 1 h, the solvent is removed, and the residue, which is uniform according to 1H-NMR, is employed in the subsequent reaction without further purification. Yield: 59 g (181 mmol), 70% of theory, purity according to 1H-NMR about 96%.

Workup

  1. additionare added dropwise
  2. customthe solvent is removed
  3. customis employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-163c499d37484a9ba4df73263ed3232e
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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