Triethylamine → HCID 76568138, compound

HRID 1728140Notes

Reaction equation

HRID 1728140 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[CH:9]1[C:14]2([C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:24])[CH:13]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[CH2:12][C:11](=[O:32])[NH:10]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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:37]#[CH:38])=[CH:4][C:3]=1[CH:9]1[C:14]2([C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:24])[CH:13]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[CH2:12][C:11](=[O:32])[NH:10]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 76567880HCID 76567880, compound

Product 1

HCID 76568138HCID 76568138, compoundYield 149.9%

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)-2′-(2-amino-5-iodophenyl)-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in example 203 (0.2 g, 0.35 mmol) was reacted with trimethylsilyl acetylene (68 mg, 0.69 mmol), CuI (0.13 g, 0.69 mmol), triethylamine (70 mg, 0.69 mmol), and dichlorobis(triphenylphosphine)palladium (49 mg, 0.069 mmol) in anhydrous tetrahydrofuran, and then treated with aqueous NaOH in methanol to give racemic (2′R,3R,4′S)-2′-(2-amino-5-ethynylphenyl)-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.25 g, 84%)

Sources & evidence

ORD record
ord-51da22b4afe34aea92c237a64bd2bdd5
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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