Water → Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

HRID 1066177Notes

Reaction equation

HRID 1066177 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:35]=[CH:34][C:14]([C:15]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:18]=3)=[O:16])=[CH:13][C:12]=2O)=[CH:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-:38].[K+].[K+].[Cl:43][CH:44](Br)[CH2:45][CH3:46].O>CN(C)C=O.C(OCC)(=O)C>[Cl:43][CH2:44][CH2:45][CH2:46][O:38][C:13]1[CH:12]=[C:11]([NH:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH:35]=[CH:34][C:14]=1[C:15]([C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:18]=1)=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 21197979Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl)indol-1-yl}butanoate

Product 1

HCID 21197980Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl]indol-1-yl}butanoate (39.3 g) was dissolved in N,N-dimethylformamide (200 ml), and potassium carbonate (22.4 g) and chlorobromopropane (24 ml) were added to the solution. The mixture was stirred at room temperature for four hours. The reaction mixture was poured into water, and ethyl acetate was further added for extraction. The formed organic layer was sequentially washed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine, and dried. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby obtain 44.8 g of ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate as a yellow oil. MS(m/z): 562(MH+); IR(CHCl3)cm−1:3450, 1730, 1595; NMR(CDCl3)δ:1.21(t, 3H), 1.25(t, 3H), 2.13˜2.36(m, 6H), 2.66(q, 2H), 3.72(t, 2H), 4.10(q, 2H), 4.21˜4.31(m, 4H), 4.43(d, 2H), 5.03(t, 1H), 6.59(d, 1H), 7.08˜7.50(m, 9H), 7.60(s, 1H), 8.31˜8.37(m, 1H).

Workup

  1. additionwas further added for extraction
  2. washThe formed organic layer was sequentially washed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f04b72c3d9404e88863adc4b743dbfdd
Source dataset
uspto-grants-2001_06
Patent number
US06242449B1

Reaction notes

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