(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → 3-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 24335Notes

Reaction equation

HRID 24335 reaction equation
C([Li])CCC.[Br-].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(NCC)C.[Li].[CH2:37]([O:39][C:40]([C:42]1[NH:43][C:44]2[C:49]([C:50]=1[CH:51]=O)=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH3:38]>C1COCC1>[CH2:37]([O:39][C:40]([C:42]1[NH:43][C:44]2[C:49]([C:50]=1[CH:51]=[CH:10][CH2:9][N:8]([CH3:30])[CH3:7])=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH3:38]

Participants

6

Reactant 4

HCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylateHCID 45051810Lithium diethylamineHCID 178418339Butyllithium

Product 1

HCID 543568283-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (1.1 equiv.) was added to a suspension of (2-dimethylaminoethyl)triphenylphosphonium bromide in THF (0.2 M) at 0° C. After stirring for 30 minutes, lithium diethylamine (1.1 equiv.) was added dropwise followed by the cold suspension of 3-formyl-1H-indole-2-carboxylic acid ethyl ester (3.96 g, 18.2 mmol) in THF. The resulting orange suspension was stirred for 18 hours. The reaction was then quenched with saturated ammonium chloride and extracted with 10% MeOH in DCM. The organic layer was washed with saturated sodium bicarbonate, dried and concentrated to give 3-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester as a brownish-red waxy solid.

Workup

  1. stirringThe resulting orange suspension was stirred for 18 hours
  2. customThe reaction was then quenched with saturated ammonium chloride
  3. extractionextracted with 10% MeOH in DCM
  4. washThe organic layer was washed with saturated sodium bicarbonate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bef9feba2e844741aa8e3640f2b05a5a
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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