Triethylamine → HCID 67255828, compound

HRID 1672355Notes

Reaction equation

HRID 1672355 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:22])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:13](=[O:22])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 66827Phenylboronic Acid2×HCID 67255446HCID 67255446, compound

Product 1

HCID 67255828HCID 67255828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.13 mmol) of 8-bromo-1-(2-chloro-phenyl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one [see under B)], 48.8 mg (0.40 mmol) of phenylboronic acid (Fluka, Buchs, Switzerland), 53 mg (0.27 mmol) of cupric acetate anhydrous (Fluka, Buchs, Switzerland) and 56 μl (0.4 mmol) of triethylamine are dissolved in 1 ml of anhydrous dichloromethane and the suspension is stirred for 16 h at room temperature. After this time, additional phenylboronic acid (24 mg), cupric acetate anhydrous (27 mg) and triethylamine (28 μl) are added and the suspension is stirred at room temperature for 24 h. The suspension is evaporated to dryness and the crude compound is purified by clash chromatography (dichloromethan with 0.5% of methanol) to obtain the title compound: Analytical HPLC: tret=8.22 min (Grad. 2); ES-MS: m/e0=449.9. 451.9.

Workup

  1. stirringthe suspension is stirred at room temperature for 24 h
  2. customThe suspension is evaporated to dryness
  3. customthe crude compound is purified by clash chromatography (dichloromethan with 0.5% of methanol)

Sources & evidence

ORD record
ord-8f6c172b7382448bae368510b158c7d7
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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