1-Chloro-3-iodobenzene → Tert-butyl 3-[2-(3-chlorophenyl)ethynyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylate

HRID 2040850Notes

Reaction equation

HRID 2040850 reaction equation
CC1N=C(N2CCC(=C)CC2)[C:5]([N+:15]([O-])=[O:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](I)[CH:20]=1.C=C1CCN(C2C([N+]([O-])=O)=CC=CN=2)CC1.[CH2:42]=[C:43]1[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]1>>[Cl:18][C:19]1[CH:20]=[C:21]([C:3]#[C:4][C:5]2[CH2:42][C:43]3([CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]3)[O:16][N:15]=2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 122691-Chloro-3-iodobenzeneHCID 27568081-Boc-4-MethylenepiperidineHCID 574938092-(4-Methylene-1-piperidyl)-3-nitropyridineHCID 574938106-Methyl-2-(4-methylene-1-piperidyl)-3-nitropyridine

Product 1

HCID 57493815Tert-butyl 3-[2-(3-chlorophenyl)ethynyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylate

Procedure

The title compound was synthesized following the method reported for the compound of Example 3, substituting 2-bromo-6-methylpyridine with 1-chloro-3-iodobenzene and Compound 3c with Compound 2a, with tert-butyl 4-methylenepiperidine-1-carboxylate. After the usual work-up, the crude was purified by automated flash chromatography (SP1®TM -Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 6:4) affording the title product as white solid. Yield: 76.9%.

Workup

  1. customThe title compound was synthesized
  2. customAfter the usual work-up, the crude was purified by automated flash chromatography (SP1®TM -Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 6:4)

Sources & evidence

ORD record
ord-a0aee53bc3154901b7a8134f5da7d754
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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