Trimethylsilylacetylene → HCID 66854789, compound

HRID 252120Notes

Reaction equation

HRID 252120 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][N:13]=2)[CH2:8]1.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>ClCCl.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[CH:14][N:13]=2)[CH2:8]1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 66854640HCID 66854640, compound

Product 1

HCID 66854789HCID 66854789, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Dissolve (S)-(2,4-dichlorobenzyl)-[1-(5-iodopyridin-2-yl)-pyrrolidin-3-yl]-amine hydrochloride (250 mg, 0.52 mmol) in dichloromethane (15 mL) and triethylamine (10 mL). Add trans-dichlorobis(triphenylphosphine)palladium (II) (24 mg, 0.034 mmol), copper (I) iodide (6 mg, 0.032 mmol) and (trimethylsilyl)acetylene (370 μL, 2.62 mmol). Stir the mixture at room temperature for 1 h, filter through a pad of Celite®, concentrate and chromatograph on silica gel, eluting with a gradient of 20:80 to 1:1 ethyl acetate:hexanes, to give (S)-(2,4-dichlorobenzyl)-[1-(5-trimethylsilanylethynyl-pyridin-2-yl)-pyrrolidin-3-yl]-amine as a yellow oil (190 mg, 88%). MS (ES): m/z=418 [M+H].

Workup

  1. filtrationfilter through a pad of Celite®
  2. concentrationconcentrate
  3. washchromatograph on silica gel, eluting with a gradient of 20:80 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-f3efa61a33d84d559c6055cc8a5966b2
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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