Sodium Carbonate → HCID 178450361, compound

HRID 2192966Notes

Reaction equation

Br[C:2]1[CH:21]=[CH:20][C:5]2[C:6]([OH:19])=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:11]=[CH:10][CH:9]=3.[CH3:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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.O>[CH2:15]([O:14][C:12]1[N:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C:4]1[CH:3]=[C:2]([C:26]3[CH:25]=[N:24][N:23]([CH3:22])[CH:27]=3)[CH:21]=[CH:20][C:5]=1[C:6]([OH:19])=[N:7]2)[CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 135 °C

Procedure

To a mixture of 9-bromo-1-butoxybenzo[c]-1,6-naphthyridin-6-ol (251 mg, 0.723 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (256 mg, 1.229 mmol), lithium chloride (184 mg, 4.34 mmol), and tetrakis(triphenylphosphine)palladium (251 mg, 0.217 mmol) in DMF (7229 μl) in a sealed tube, sodium carbonate (3615 μl, 7.23 mmol, 2 M) was added, and the reaction mixture was heated to 135° C. After 2 h, the reaction mixture was allowed to cool to room temperature and poured into water. This mixture was then filtered through a frit. The filter cake was washed with dichloromethane. The filter cake was then collected and dried under high vacuum to afford 1-butoxy-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridin-6-ol as a white solid. LRMS (APCI) calc'd for (C20H21N4O2) [M+H]+, 349.2; found 349.1.

Workup

temperatureto cool to room temperature
filtrationThis mixture was then filtered through a frit
washThe filter cake was washed with dichloromethane
customThe filter cake was then collected
customdried under high vacuum

Sources & evidence

ORD record: ord-73cdb01bd53b4bcf8ee2ca601a8d5924
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329722B2

Reaction notes

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