Trimethyl borate → 8,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

HRID 1485592Notes

Reaction equation

HRID 1485592 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]2([CH3:23])[CH3:22])[CH:15]=1.C([Li])CCC.[B:29](OC)([O:32]C)[O:30]C>C1COCC1.C1CCCCC1>[CH3:22][C:5]1([CH3:23])[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=3)[CH:15]=[C:2]([B:29]([OH:32])[OH:30])[CH:3]=2

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 671097356-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridineHCID 178418339Butyllithium

Product 1

HCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

93.7 g (259 mmol) of 6-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine (Br-1) 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, the solvent is removed, and the residue, which is uniform according to 1H-NMR, is employed without further purification in the subsequent reaction. 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 without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-dccd6288fd7f45f3a1671afa16ebe730
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

Loading…