Triethylamine → 3-Butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357280Notes

Reaction equation

HRID 1357280 reaction equation
[CH2:1]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14](Cl)=[O:15])[CH2:2][CH2:3][CH3:4].[Br:17][C:18]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH2:30][NH:31][CH3:32])=[CH:23]2.C(N(CC)CC)C>C(Cl)Cl>[Br:17][C:18]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH2:30][N:31]([CH3:32])[C:14]([C:6]1[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4])=[O:15])=[CH:23]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18505315(5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amineHCID 185053603-Butyl-benzofuran-2-carbonyl chloride

Product 1

HCID 865873943-Butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-butyl-benzofuran-2-carbonyl chloride (9.0 mmol), prepared in the previous step, in 50 mL of methylene chloride was added under nitrogen dropwise over 2 h to a solution of (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine (2.52 g, 9.0 mmol), prepared in step 7 of Example 36, and triethylamine (1.26 mmol, 9.0 mmol) in 250 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature overnight. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure to 4.13 g of a residue. Purification of the residue on 500 g of silica gel (230-400 mesh) using 90% hexane-methylene chloride to 5% EtOAc-methylene chloride as the eluents gave 3-butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide as a clear oil, MS m/z: 480 [M+H]+.

Workup

  1. additionAfter the addition the reaction
  2. extractionThe reaction was extracted with 1 N HCl, 5% NaHCO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure to 4.13 g of a residue
  5. customPurification of the residue on 500 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-e97e2d23b853455bbd15030004bb30d4
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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