HCID 67235911, compound → HCID 67235947, compound

HRID 1039030Notes

Reaction equation

HRID 1039030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([Br:22])[CH:19]=[CH:18][C:17]=2[NH2:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.CN(C)C=O>[Br:22][C:20]1[CH:21]=[C:16]2[C:17](=[CH:18][CH:19]=1)[NH:23][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]1)=[CH:15]2

Participants

4

Reactant 1

HCID 67235911HCID 67235911, compound

Product 1

HCID 67235947HCID 67235947, compound

Reagents, catalysts & solvents 2

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A 250 mL round bottom flask was charged with 4-(2-amino-5-bromo-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl ester (5.90 g, 15.6 mmol), dichlorobis(benzonitrile)palladium (II) (1.20 g, 3.13 mmol), and dimethylformamide (175 mL) and the resulting mixture heated to 80° C. for 24 h. The resulting mixture was then concentrated in-vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-80:20 Heptane:EtOAc) to yield tert-butyl 4-(5-bromo-1H-indol-2-yl)piperidine-1-carboxylate. 1H NMR (300 MHz, CDCl3) δ 7.66 (s, 1H), 7.16-7.23 (m, 2H), 6.20 (s, 1H), 2.84-3.02 (m, 5H), 1.97-2.04 (m, 2H), 1.61-1.74 (m, 2H), and 1.48 (s, 9H); MS (ES+) 380 (M+1).

Workup

  1. concentrationThe resulting mixture was then concentrated in-vacuo
  2. customthe residue purified via flash silica gel chromatography (Analogix IF-280

Sources & evidence

ORD record
ord-f7193d98aaf441a6842fa0aaa3c18894
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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