Water → HCID 131729798, compound

HRID 1510229Notes

Reaction equation

[CH2:1]([C@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C(COC)OC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:22]([O:21][C:20](=[O:26])[NH:19][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9](=[O:10])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)=[CH:14][CH:13]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of tert-butyl {(1S)-1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl}carbamate (1.0 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (587 mg) and potassium phosphate (1.52 g) in dimethoxyethane (30 mL) was added 1,1′-bis(diphenylphosphino)ferrocene palladium(II) chloride (58 mg) and the mixture was stirred at 120° C. for 4 hours. Water was added and the mixture was extracted with chloroform. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl[(1S)-1-benzyl-2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl]carbamate (830 mg).

Workup

extractionthe mixture was extracted with chloroform
washThe separated organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-4670aaeac54247f6a07dd80b87a4f2f2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211919B2

Reaction notes

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