Sodium Carbonate → HCID 66760917, compound

HRID 561832

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:16][O:17][CH2:18]/[CH:19]=[CH:20]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:3]=[C:2](/[CH:20]=[CH:19]/[CH2:18][O:17][CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH:11]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-N-cyclopropyl-6-methoxyisonicotinamide from the previous step (1 eq.) in DMF (0.3 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 3 eq.). The resulting suspension was heated at 100° C. for 7 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 brown tar. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) followed by recrystallization from Hex:ether afforded the title compound as a white solid.

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 brown tar
customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)
customfollowed by recrystallization from Hex

Sources & evidence

ORD record: ord-b9f2faf003814cd486e079bdd716ec80
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063105B2

Linked notes

Loading…