Triethylamine → HCID 76568007, compound

HRID 1728135Notes

Reaction equation

HRID 1728135 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:32])[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]=[CH:26][C:25]=3[CH3:31])[C:5]2=[CH:4][CH:3]=1.C[Si]([C:37]#[CH:38])(C)C.C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.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:32])[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:37]#[CH:38])[CH:27]=[CH:26][C:25]=3[CH3:31])[C:5]2=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 76568163HCID 76568163, compound

Product 1

HCID 76568007HCID 76568007, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 193, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-iodo-2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in example 198c (0.27 g, 0.47 mmol) was reacted with trimethylsilyl acetylene (92 mg, 0.94 mmol), CuI (0.18 g, 0.94 mmol), triethylamine (95 mg, 0.94 mmol), and dichlorobis(triphenylphosphine)palladium (66 mg, 0.094 mmol) in anhydrous tetrahydrofuran, 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-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.12 g, 54%)

Sources & evidence

ORD record
ord-03cec31e424c4e5b9676e329cad6802c
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…