Triethylamine → HCID 86615273, compound

HRID 1445131Notes

Reaction equation

HRID 1445131 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([N:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]3)[N:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[C:10]([CH3:28])=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:31]=1.C#C.C[SiH](C)C.C(N(CC)CC)C>CN(C)C=O.[Cu]I>[ClH:17].[CH2:1]([N:8]1[C:12]2=[C:13]([N:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]3)[N:14]=[C:15]([C:30]#[CH:31])[CH:16]=[C:11]2[C:10]([CH3:28])=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86615272HCID 86615272, compoundHCID 131727893HCID 131727893, compound

Product 1

HCID 86615273HCID 86615273, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-benzyl-5-chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.24 mmol) prepared in Example 658, bis(triphenylphosphine)palladium chloride(II) (9.4 mg, 0.013 mmol), triphenylphosphine (12.6 mg, 0.48 mmol), copper(I) iodide (2.5 mg, 0.013 mmol), trimethylsilane acetylene (42 μl, 0.3 mmol), and triethylamine (1 ml) in anhydrous N,N-dimethylformamide (2 ml) was refluxed for 8 hours at 120° C. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 32.1 mg of the titled compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5
  3. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8a6b6edc6e044707ad2aa1629b81c138
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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