Triethylamine → HCID 74931580, compound

HRID 1095126Notes

Reaction equation

HRID 1095126 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[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[O:31][C:32]3[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([CH3:39])[CH:33]=3)[C:5]2=[CH:4][CH:3]=1.C[Si]([C:45]#[CH:46])(C)C.C(N(CC)CC)C.[OH-].[Na+]>CN(C)C=O.CO.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[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:45]#[CH:46])[CH:27]=[CH:26][C:25]=3[O:31][C:32]3[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([CH3:39])[CH:33]=3)[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 131729502HCID 131729502, compound

Product 1

HCID 74931580HCID 74931580, compoundYield 53.4%

Reagents, catalysts & solvents 3

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

Procedure

In a manner similar to the method described in example 6a, racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(2,6-dimethyl-4-pyridinyloxy)-5-iodo-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.62 g, 0.9 mmol) was reacted with trimethylsilyl acetylene (0.89 g, 9 mmol), CuI (5 mg), triethylamine (2.74 g, 27 mmol), and dichlorobis(triphenylphosphine) palladium (0) (50.7 mg, 0.07 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′-[2-(2,6-dimethyl-4-pyridinyloxy)-5-ethynyl-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a pale yellow solid (Yield 0.28 g, 53%)

Sources & evidence

ORD record
ord-da14b877f4f14dada6109e4ac0f5a15e
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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