Trimethyl borate → 8,8-Dimethyl-8H-indolo[3,2,1-de]acridine-3-boronic acid

HRID 523039Notes

Reaction equation

HRID 523039 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([CH3:23])([CH3:22])[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:4]=2[CH:3]=1.C([Li])CCC.[B:29](OC)([O:32]C)[O:30]C>C1COCC1.C1CCCCC1>[CH3:22][C:15]1([CH3:23])[C:14]2[C:9]3=[C:10]([C:4]4[CH:3]=[C:2]([B:29]([OH:32])[OH:30])[CH:7]=[CH:6][C:5]=4[N:8]3[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=3)[CH:11]=[CH:12][CH:13]=2

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 671095853-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridineHCID 178418339Butyllithium

Product 1

HCID 672041848,8-Dimethyl-8H-indolo[3,2,1-de]acridine-3-boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

93.9 g (259 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine 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., and, after 1 h, 37 ml of trimethyl borate (336 mmol) are added dropwise. The mixture is allowed to come to room temperature over the course of 1 h, and the solvent is removed. The residue, which is uniform according to 1H-NMR, is employed in the subsequent reaction without further purification. The yield is 77 g (235 mmol), corresponding to 91% of theory.

Workup

  1. customto come to room temperature over the course of 1 h
  2. customthe solvent is removed
  3. customis employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-d718dbf87a784dba9163df0655fe3f34
Source dataset
uspto-grants-2016_05
Patent number
US09334260B2

Reaction notes

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