Triethylamine → HCID 178451206, compound

HRID 343405Notes

Reaction equation

HRID 343405 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19](Br)=[CH:20][CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([CH:38]=[CH2:39])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35](/[CH:38]=[CH:39]/[C:19]2[CH:18]=[C:17]3[C:22]([C:14]([CH:11]4[CH2:12][CH2:13][N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])[CH2:9][CH2:10]4)=[N:15][NH:16]3)=[CH:21][CH:20]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 10910832tert-Butyl 4-ethenylpiperidine-1-carboxylateHCID 178451205HCID 178451205, compound

Product 1

HCID 178451206HCID 178451206, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of [4-(6-bromo-1H-indazol-3-yl)-piperidin-1-yl]-acetic acid tert butyl ester (1.34 g, 3.40 mmol), 4-vinyl-piperidine-1-carboxylic acid tert-butyl ester (0.75 g, 3.57 mmol), triethylamine (1.4 ml, 10.2 mmol), palladium (ii) acetate (0.050 g, 0.22 mmol) and tri(o-tolyl)phosphine (0.210 g, 0.6 mmol) in DMF (60 ml) was stirred at 120° under nitrogen for 16 h. The mixture was evaporated in vacuo and purified by flash chromatography on silica gel (Merck 9385), eluant ethyl acetate:cyclohexane:triethylamine (50:50:2→100:0:2), to give the title compound as a yellow solid (1.18 g, 66%).

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by flash chromatography on silica gel (Merck 9385), eluant ethyl acetate:cyclohexane:triethylamine (50:50:2→100:0:2)

Sources & evidence

ORD record
ord-0795edb640254795bf277f0dca62f4f0
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

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