Ethyl Acetate → HCID 67114180, compound

HRID 1968872Notes

Reaction equation

HRID 1968872 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([CH2:13][N:14]([C:27]2[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=2)[C:15]([C@@H:17]2[CH2:19][C@H:18]2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].CCO[C:44]([CH3:46])=O.[CH3:47][C:48]#N.O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([CH2:13][N:14]([C:15]([C@@H:17]2[CH2:19][C@H:18]2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=2)=[O:16])[C:27]2[CH:32]=[CH:31][C:30]([C:8]3[CH:12]=[CH:11][C:48]([CH2:47][CH2:44][CH3:46])=[CH:10][CH:9]=3)=[CH:29][CH:28]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18373917Acetonitrile--water (1/1)HCID 67114202HCID 67114202, compound

Product 1

HCID 67114180HCID 67114180, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of [1-({(4-Bromo-phenyl)-[trans-2-(6-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-cyclopentyl]-carbamic acid t-butyl ester (95 mg, 0.18 mmol), arylboronic acid (0.22 mmol), Pd(PPh3)2Cl2 (14 mg, 0.02 mmol) and K2CO3 (47 mg, 0.34 mmol) in CH3CN/H2O (3.5/0.5 mL) was macrowaved at 140° C. for 20 min. The reaction mixture was passed through a short silica pad (EtOAc) and concentrated. The residue was subjected to ISCO (12 g column, 0-50% EtOAc in hexaneover 25 min) to give the desired products. MS (MH+ 572).

Workup

  1. concentrationconcentrated
  2. customwas subjected to ISCO (12 g column, 0-50% EtOAc in hexaneover 25 min)

Sources & evidence

ORD record
ord-1ba6a735089947659bf073a507b92db7
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

Loading…