tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]carbamate → tert-butyl-N-[1-[[5-cyclopentyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

HRID 535420Notes

Reaction equation

HRID 535420 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].Br[Zn][CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86694405tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]carbamateHCID 178419769HCID 178419769, compound

Product 1

HCID 86694409tert-butyl-N-[1-[[5-cyclopentyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate C2d (60 mg, 0.14 mmol), bromo(cyclopentyl)zinc (0.5 M solution in THF, 1.6 ml, 0.81 mmol), Palladium(II) acetate (1.5 mg, 0.01 mmol), 2-Dicyclohexyl-phosphino-2′,4′,6′-triisopropylbiphenyl (6.4 mg, 0.01 mmol) in toluene (0.25 ml) is stirred at RT for 6 days. The reaction mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 18 mg (31%). HPLC-MS: M+H=434; tR=1.97 min (*Method—5).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-f5405ee784684b10977667f30ee5e43c
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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