Sodium hydride → (E)-3-[1-(4-Dimethylamino-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 870090Notes

Reaction equation

HRID 870090 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][NH:13][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:17][N:18]([CH3:29])[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][N:13]([S:25]([C:22]2[CH:21]=[CH:20][C:19]([N:18]([CH3:29])[CH3:17])=[CH:24][CH:23]=2)(=[O:27])=[O:26])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 125069434-(Dimethylamino)benzene-1-sulfonyl chlorideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate2×

Product 1

HCID 66646108(E)-3-[1-(4-Dimethylamino-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Procedure

Starting materials: sodium hydride 60% (0.031 g), (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester (compound D1) (0.100 g), 4-dimethylamino-benzenesulfonyl chloride (0.145 g). Reaction conditions: 30° C., 45 min; −30° C., 2.5 hours.

Workup

  1. customReaction conditions
  2. custom30° C., 45 min
  3. custom−30° C., 2.5 hours

Sources & evidence

ORD record
ord-052a71d4ac234d529eeccd7865ed28d6
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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