Trimethyl borate → HCID 67326151, compound

HRID 2277351Notes

Reaction equation

HRID 2277351 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[C:29]4[CH:28]=[CH:27][C:26]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][C:24]=4[C:8]4[CH:9]=[C:10]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:11]=[C:12]([C:13]([CH3:17])([CH3:16])[C:14]=2[CH:15]=1)[C:7]3=4.C([Li])CCC.[B:41]([O:46]C)(OC)[O:42]C>C1COCC1.C1CCCCC1>[CH3:16][C:13]1([CH3:17])[C:12]2[C:7]3=[C:8]([C:24]4[CH:25]=[C:26]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:27]=[CH:28][C:29]=4[N:6]3[C:5]3[CH:4]=[CH:3][C:2]([B:41]([OH:46])[OH:42])=[CH:15][C:14]1=3)[CH:9]=[C:10]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:11]=2

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 67325759HCID 67325759, compoundHCID 178418339Butyllithium

Product 1

HCID 67326151HCID 67326151, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

133 g (259 mmol) of 10-bromo-8,8-dimethyl-3,6-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., 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. additionare added dropwise
  2. customthe solvent is removed
  3. customis employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-225c5ad121ac4fafa631eaa44b86803a
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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