Triethylamine → HCID 74931579, compound

HRID 1095124Notes

Reaction equation

HRID 1095124 reaction equation
[C:1]([C:4]1[CH:41]=[CH:40][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12](I)=[CH:11][C:10]=2[CH:16]2[C:21]3([C:29]4[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=4)[NH:23][C:22]3=[O:31])[CH:20]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=3)[CH2:19][C:18](=[O:39])[NH:17]2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C[Si]([C:46]#[CH:47])(C)C.C(N(CC)CC)C.[OH-].[Na+]>CN(C)C=O.CO.[Cu]I>[C:1]([C:4]1[CH:41]=[CH:40][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:46]#[CH:47])=[CH:11][C:10]=2[CH:16]2[C:21]3([C:29]4[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=4)[NH:23][C:22]3=[O:31])[CH:20]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=3)[CH2:19][C:18](=[O:39])[NH:17]2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 74931578HCID 74931578, compound

Product 1

HCID 74931579HCID 74931579, compound

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)-2′-[2-(4-carbamoyl-phenoxy)-5-iodo-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.35 g, 0.5 mmol) was reacted with trimethylsilyl acetylene (0.49 g, 5 mmol), CuI (3 mg), triethylamine (1.52 mL, 15 mmol), and dichlorobis(triphenylphosphine) palladium (0) (28 mg, 0.04 mmol) in anhydrous N,N-dimethylformamide, and then treated with aqueous NaOH in methanol to give racemic(2′R, 3R, 4′S)-2′-[2-(4-carbamoyl-phenoxy)-5-ethynyl-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an off white solid (Yield 0.25 g, 84%)

Sources & evidence

ORD record
ord-917de85d24864648b345afc4c825c653
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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