Triethylamine → HCID 68894353, compound

HRID 1437160Notes

Reaction equation

HRID 1437160 reaction equation
C(N(CC)CC)C.[O:8]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:15]2)=[CH:9]1.[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]Br)[CH:33]=1>ClCCl>[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:26]2[CH2:25][CH2:24][CH:23]([C:16]3[C:17]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=4)[N:14]([CH2:13][C:10]4[CH:11]=[CH:12][O:8][CH:9]=4)[CH:15]=3)[CH2:28][CH2:27]2)[CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 68896318HCID 68896318, compound

Product 1

HCID 68894353HCID 68894353, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.3 ml of triethylamine were added over a solution of 0.4 g (1.42 mmol) of 1-furan-3-ylmethyl-3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine in 5 ml of dichloromethane. A solution of 0.39 g (1.71 mmol) of 3-bromomethyl-benzoic acid methyl ester in 2 ml of dichloromethane was added and the crude mixture was stirred at room temperature for 18 hours. The mixture was diluted with 25 ml of dichloromethane and it was washed with water and brine. The organic phase was dried over magnesium sulphate and after filtration and evaporation, 0.53 g of the crude residue were obtained. The crude mixture was purified by flash chromatography over silica gel affording 0.3 g (49% of yield) of the expected product.

Workup

  1. washwas washed with water and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationafter filtration and evaporation

Sources & evidence

ORD record
ord-2c8129a5764f4f72ac3a090a15236807
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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