Triethylamine → HCID 76567932, compound

HRID 1728132Notes

Reaction equation

HRID 1728132 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:37])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28](I)[CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[O:33][CH2:34][CH2:35][OH:36])[C:5]2=[CH:4][CH:3]=1.C[Si]([C:42]#[CH:43])(C)C.C(N(CC)CC)C.[OH-].[Na+]>CN(C)C=O.CO.[Cu]I.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>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:37])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([C:42]#[CH:43])[CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[O:33][CH2:34][CH2:35][OH:36])[C:5]2=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 76568159HCID 76568159, compound

Product 1

HCID 76567932HCID 76567932, compoundYield 11%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 193, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(2-hydroxy-ethoxy)-5-iodo-3-methoxy-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in example 196c (0.3 g, 0.46 mmol) was reacted with trimethylsilyl acetylene (0.65 mL, 4.6 mmol), CuI (10 mg), triethylamine (1.9 mL, 13.8 mmol), and dichlorobis(triphenylphosphine)palladium (32 mg, 0.046 mmol) in anhydrous N,N-dimethylformamide, and then treated with aqueous NaOH in methanol to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-ethynyl-2-(2-hydroxy-ethoxy)-3-methoxy-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a light brown solid (Yield 28 mg).

Sources & evidence

ORD record
ord-ffce3d098da04b168db52ba9bff7e2cb
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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