Triethylamine → HCID 22461302, compound

HRID 1937626Notes

Reaction equation

HRID 1937626 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=2[C:4](=[O:13])[CH2:3]1.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:14][C:2]1([CH3:1])[CH2:10][C:9]2[N:8]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([F:15])[CH:21]=3)[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=2[C:4](=[O:13])[CH2:3]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 27339863-Fluorophenylboronic acidHCID 22461260HCID 22461260, compound

Product 1

HCID 22461302HCID 22461302, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

6,6-Dimethyl-3-ethyl-4,5,6,7-tetrahydro-1H-indol-4-one (50 mg, 0.26 mmol), copper acetate (71 mg, 0.39 mmol), 3-fluorophenyl boronic acid (73 mg, 0.52 mmol) and triethylamine (73 μL, 0.52 mmol) and triethylamine (73 μL, 0.52 mmol) in DCM (1 mL) was stirred at room temperature for 48 h. The crude reaction mixture was poured onto a bond elut tube (Anachem 1225-6034 10 g/60 mL) and eluted using isohexane : EtOAc (100:0→5:1) to afford a yellow solid. The solid was triturated in ether to afford the title compound (15 mg, 20%) as a colourless solid. 1H NMR (360 MHz, CDCl3) δ 1.08 (6H,s), 1.22 (3H,t, J=7.4Hz), 2.36 (2H,s), 2.62 (2H,s), 2.81 (2H,q, J=7.4 Hz), 6.57 (1H,s), 7.02-7.11 (3H,m), 7.41-7.45 (1H,m). MS (ES+) 286 (M+1).

Workup

  1. customThe crude reaction mixture
  2. washeluted
  3. customto afford a yellow solid
  4. customThe solid was triturated in ether

Sources & evidence

ORD record
ord-a945051d000740edb1c15e4a5ce9e6b1
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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