1,1'-Carbonyldiimidazole → Methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1904472Notes

Reaction equation

HRID 1904472 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][N:29]2[CH2:32][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][C:34]=2[O:43][CH3:44])=[CH:25][CH:24]=1>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([CH2:6][C:7]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[CH:28][N:29]3[CH2:32][C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][C:34]=3[O:43][CH3:44])=[CH:25][CH:24]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 71606Cyclopentylacetic acidHCID 14708762Methyl 4-(6-aminoindol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 19744328Methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of cyclopentylacetic acid (0.24 ml) and 1,1'-carbonyldiimidazole (0.34 g) in methylene chloride (3 ml) was heated under reflux for 30 minutes and then treated with a solution of ester (B) (0.5 g) in methylene chloride (3 ml). The mixture was heated under reflux for 30 minutes, stirred at room temperature for 24 hours, and then diluted with ethyl acetate. This organic solution was washed sequentially with 10% v/v hydrochloric acid, water, and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on a 6×18 cm silica gel column using 99:1 v/v ethyl acetate:toluene as the eluent followed by recrystallization from hexane/ethyl acetate to give methyl 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoate (P) as a solid; partial NMR: 2.0-2.5(br m, 3H, CH2CH), 3.9(s, 3H, OCH3), 4.0(s, 3H, OCH3), 5.3(s, 2H, NCH2).

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. washThis organic solution was washed sequentially with 10% v/v hydrochloric acid, water, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on a 6×18 cm silica gel column
  8. customtoluene as the eluent followed by recrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-370fdd4173bc478f83061eb0575925a1
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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