Picolyl chloride hydrochloride → HCID 11353926, compound

HRID 2301675Notes

Reaction equation

HRID 2301675 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Cl.[H-].[K+].[CH:12]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[C:27]([CH2:35][CH2:36][O:37][C:38]2[CH:48]=[CH:47][C:41]([C:42]([O:44]CC)=[O:43])=[CH:40][CH:39]=2)=[C:26]1[CH2:49][OH:50])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH:12]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[C:27]([CH2:35][CH2:36][O:37][C:38]2[CH:48]=[CH:47][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[C:26]1[CH2:49][O:50][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 82127Potassium hydrideHCID 18373263HCID 18373263, compound

Product 1

HCID 11353926HCID 11353926, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Picolyl chloride hydrochloride (164 mg, 1 mmol) was added to potassium hydride (228 mg of 40% KH, 2 mmol, in mineral oil, washed with hexanes) in 5 mL of dry N,N-dimethylformamide at room temperature. Ethyl 4-{2-[1-benzhydryl-5-chloro-2-(hydroxymethyl)-1H-indol-3-yl]ethoxy}benzoate (140 mg, 0.25 mmol) in 3 mL of N,N-dimethylformamide was added via syringe. After stirring at room temperature for 2 hours, the reaction was quenched with iced water, extracted with CH2Cl2, dried over magnesium sulfate and purified by preparative thin layer chromatography (20% methanol/CH2Cl2 as the developing solvents) to yield 16 mg (11%) of the desired product as a pale yellow solid. m/z (M−1) 600.9.

Workup

  1. customthe reaction was quenched with iced water
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over magnesium sulfate
  4. custompurified by preparative thin layer chromatography (20% methanol/CH2Cl2 as the developing solvents)

Sources & evidence

ORD record
ord-3f88ea5127a2433fa0f55a5bdb3a6dab
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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