Triethylamine → HCID 86631793, compound

HRID 1095110Notes

Reaction equation

HRID 1095110 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:42])[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]=[CH:36][C:35]([O:38][CH2:39][CH2:40]O)=[CH:34][CH:33]=3)[C:5]2=[CH:4][CH:3]=1.C[Si]([C:47]#[CH:48])(C)C.C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.CO.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:42])[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:47]#[CH:48])[CH:27]=[CH:26][C:25]=3[O:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH3:40])=[CH:36][CH:37]=3)[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 74931482HCID 74931482, compound

Product 1

HCID 86631793HCID 86631793, compound

Reagents, catalysts & solvents 3

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

Procedure

In a manner similar to the method described in Example 2, racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-{2-[4-(2-hydroxy-ethoxy)-phenoxy]-5-iodo-phenyl}spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.9 g, 1.26 mmol) was reacted with trimethylsilyl acetylene (0.25 g, 2.5 mmol), CuI (0.48 g, 2.5 mmol), triethylamine (0.25 g, 2.5 mmol) and dichlorobis(triphenylphosphine) palladium(0) (0.18 g, 0.025 mmol) in tetrahydrofuran, then treated with aqueous NaOH solution in methanol to give racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-{5-ethynyl-2-[4-(2-ethoxy)-phenoxy]-phenyl}spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an off white solid (Yield 0.58 g, 75%).

Sources & evidence

ORD record
ord-93872c99222b461997f39aeb8665ffbf
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

Loading…