Tetrahydrofuran → HCID 67325807, compound

HRID 2277350Notes

Reaction equation

HRID 2277350 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[C:18](C5C=CC=CC=5)[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([CH3:29])[CH3:28])[CH:15]=1.[CH2:30]([Li])[CH2:31][CH2:32][CH3:33].[B:35]([O:40]C)(OC)[O:36]C.[CH2:42]1COC[CH2:43]1>C1CCCCC1>[CH3:29][C:5]1([CH3:28])[C:4]2[C:13]3=[C:14]([C:6]4[CH:7]=[C:8]([B:35]([OH:40])[OH:36])[CH:9]=[CH:10][C:11]=4[N:12]3[C:21]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]1=3)[CH:15]=[C:2]([C:30]1[CH:43]=[CH:42][CH:33]=[CH:32][CH:31]=1)[CH:3]=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 67325930HCID 67325930, compoundHCID 178418339Butyllithium

Product 1

HCID 67325807HCID 67325807, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

113.4 g (259 mmol) of 6-bromo-8,8-dimethyl-3-phenyl-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-616bd200d7904c419957b26a747dcddb
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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