Sodium hydride → HCID 14882547, compound

HRID 330163Notes

Reaction equation

HRID 330163 reaction equation
[H-].[Na+].[O:3]=[C:4]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)/[CH:5]=[CH:6]/[C:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[CH3:30][O:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[C:35]([O:41][CH3:42])[CH:34]=1>CN(C)C=O>[O:3]=[C:4]([N:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1)/[CH:5]=[CH:6]/[C:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:19])=[CH:13][CH:14]=2)[N:9]([CH2:39][C:36]2[CH:37]=[CH:38][C:33]([C:32]([O:31][CH3:30])=[O:43])=[CH:34][C:35]=2[O:41][CH3:42])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 19870590HCID 19870590, compound

Product 1

HCID 14882547HCID 14882547, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.15 g of a 60% dispersion in mineral oil) was added to a stirred solution of E,E-3,6-di(3-oxo-3-pyrrolidino-1-propenyl)indole (0.97 g) in N,N-dimethylformamide (30 ml) cooled in an ice bath. After approximately 1 hr a solution of methyl-4-bromomethyl-3-methoxybenzoate (0.74 g) in N,N-dimethylformamide (10 ml) was added dropwise, the cooling bath was removed, and the mixture stirred for hr. The mixture was added slowly to vigorously stirred 1M hydrochloric acid (300 ml); the precipitate was isolated by filtration, washed with water and dried. The solid obtained was recrystallized from ethyl acetate to give methyl E,E-4-[3,6-di(3-oxo-3-pyrrolidino-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 76%) as an off-white powder; mp 226°-228°; partial NMR (250 MHz, DMSO-d6): 1.70°-2.0(m, 8H, pyrrolidino H), 3.40(m, 4H, pyrrolidino H), 3.65(m, 4H, pyrrolidino H), 3.83(s, 3H, OCH3), 3.95(s, 3H, OCH3), 5.50(s, 2H, NCH2Ar), 6.75(d, J=15.5 Hz, 1H, olefinic H), 7.0(m, 2H, olefinic H, and ArH).

Workup

  1. temperaturecooled in an ice bath
  2. customthe cooling bath was removed
  3. additionThe mixture was added slowly to vigorously stirred 1M hydrochloric acid (300 ml)
  4. customthe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried
  7. customThe solid obtained
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-29601fe2296f4adf9b9e486adc91e663
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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