Trimethyl borate → HCID 67109979, compound

HRID 2277359Notes

Reaction equation

HRID 2277359 reaction equation
Br[C:2]1[C:7]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[B:39]([O:44]C)(OC)[O:40]C>C1COCC1.C1CCCCC1>[C:28]1([C:15]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]3[C:9]4=[C:10]([C:6]5[CH:5]=[CH:4][CH:3]=[CH:2][C:7]=5[N:8]4[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=4)[CH:11]=[C:12]([B:39]([OH:44])[OH:40])[CH:13]=3)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 67109583HCID 67109583, compoundHCID 178418339Butyllithium

Product 1

HCID 67109979HCID 67109979, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

125.9 g (259 mmol) of bromo-8,8-diphenyl-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 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.

Workup

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

Sources & evidence

ORD record
ord-b26684142f9e4569b41fb7d9b96ca114
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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