Sodium Carbonate → HCID 66761510, compound

HRID 561834

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12](Cl)[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=CC=C[CH:30]=1.[C:48](=O)([O-])[O-:49].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[C:12](/[CH:30]=[CH:29]/[CH2:34][O:49][CH3:48])[N:13]=[C:2](/[CH:19]=[CH:18]/[CH2:17][O:16][CH3:15])[CH:3]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

customThe reaction mixture was quenched with water
extractionextracted with ether
washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
customafforded the crude product as a red oil
customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record: ord-577ce0bfa216420d91f2772d3771d42c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063105B2

Linked notes

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