Triethylamine → HCID 76567975, compound

HRID 1728148Notes

Reaction equation

HRID 1728148 reaction equation
[CH3:1][CH:2]([CH3:5])[C:3]#[CH:4].[Cl:6][C:7]1[CH:12]=[C:11]2[NH:13][C:14](=[O:40])[C:15]3([CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:19][C:18](=[O:28])[NH:17][CH:16]3[C:29]3[CH:34]=[C:33](I)[CH:32]=[CH:31][C:30]=3[O:36][CH2:37][CH2:38][OH:39])[C:10]2=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C)C=O.[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:6][C:7]1[CH:12]=[C:11]2[NH:13][C:14](=[O:40])[C:15]3([CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:19][C:18](=[O:28])[NH:17][CH:16]3[C:29]3[CH:34]=[C:33]([C:4]#[C:3][CH:2]([CH3:5])[CH3:1])[CH:32]=[CH:31][C:30]=3[O:36][CH2:37][CH2:38][OH:39])[C:10]2=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 690193-Methylbut-1-yneHCID 76567917HCID 76567917, compound

Product 1

HCID 76567975HCID 76567975, compound

Reagents, catalysts & solvents 3

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

Procedure

In a manner similar to the method described in example 209a, 3-methyl-1-butyne (0.22 g, 3.2 mmol) was used in place of 3,3-dimethyl-1-butyne to react with racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-iodo-2-(2-hydroxy-ethoxy)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.2 g, 0.32 mmol) prepared in Example 190c, CuI (3 mg), triethylamine (0.97 g, 9.6 mmol), and dichlorobis(triphenylphosphine)palladium (11.2 mg, 0.016 mmol) in anhydrous N,N-dimethylformamide to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-(3-methyl-1-butynyl)-2-(2-hydroxy-ethoxy)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a off white solid (Yield 50 mg, 28%)

Sources & evidence

ORD record
ord-f367fe1473f84af69aab2f75e6e89810
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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