Diisopropylethylamine → Piperidine, 4-(bromophenylmethylene)-1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-

HRID 606733Notes

Reaction equation

HRID 606733 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[CH3:22][O:23][C:24]1[CH:32]=[N:31][C:30]([O:33][CH3:34])=[C:29]2[C:25]=1[C:26]([C:35](=[O:39])C(O)=O)=[CH:27][NH:28]2.CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>Cl.O1CCOCC1>[Br:21][C:14](=[C:11]1[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:35]([C:26]2[C:25]3[C:29](=[C:30]([O:33][CH3:34])[N:31]=[CH:32][C:24]=3[O:23][CH3:22])[NH:28][CH:27]=2)=[O:39])[CH2:13][CH2:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 224762342-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidHCID 590345854-(1-Bromo-1-phenyl-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 5279817Piperidine, 4-(bromophenylmethylene)-1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-Yield 71%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of 4-(1-bromo-1-phenyl-methylene)-piperidine-1-carboxylic acid tert-butyl ester in 4N HCl-dioxane (10 mL) was stirred at room temperature for 2 h. The volatiles were then removed in vacuo and the residue was dissolved in CHCl3 (15 mL). To this solution was added 4,7-dimethoxy-6-azaindol-3-yl-oxoacetic acid (0.906 g, 3.37 mmol) and Hünig's base (2.40 mL, 13.8 mmol). After 5 min, BOPCl (0.950 g, 3.73 mmol) was added as a solid and the mixture was allowed to stir at room temperature for 48 hours. The reaction mixture was then adsorbed directly onto silica gel and purified by flash chromatography (SiO2/EtOAc) to give the title compound (1.101 g, 71%) as a yellow solid:

Workup

  1. customThe volatiles were then removed in vacuo
  2. dissolutionthe residue was dissolved in CHCl3 (15 mL)
  3. custompurified by flash chromatography (SiO2/EtOAc)

Sources & evidence

ORD record
ord-62b68c7e37314fe9b506a9b48bc3280a
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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