Sodium Carbonate → HCID 58994428, compound

HRID 1190093Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1Br.[C:14]1(B2OC(C)(C)C(C)(C)O2)[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 3-(4-amino-3-bromo-phenyl)-propionamide (as prepared in the previous step, 100 mg, 0.411 mmol), 2-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (94.1 mg, 0.452 mmol) and Pd(PPh3)4 (47.5 mg, 0.0411 mmol) in 3 mL of 1,4-dioxane was added 2.0 M aq Na2CO3 solution (1.64 mL, 3.29 mmol). After stirring at 80° C. for 16 h under Ar, the reaction was cooled to RT and treated with 15 mL of brine. The mixture was extracted with EtOAc (2×30 mL) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (1-3% MeOH/DCM) giving 88.1 mg (88%) of the title compound as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C15H20N2O, 245.2 (M+H). found 245.1.

Workup

temperaturethe reaction was cooled to RT
extractionThe mixture was extracted with EtOAc (2×30 mL)
dry with materialthe combined organic layers were dried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (1-3% MeOH/DCM)

Sources & evidence

ORD record: ord-d69dc175b3244aab8a33a5dcc6fe3467
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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