Sodium Bicarbonate → HCID 136501884, compound

HRID 706789Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]3=[CH:15][CH:16]=[CH:17][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.[C:33](=O)([O-])O.[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:18]([N:19]1[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:13][C:12](=[O:14])[C:11]4=[CH:15][CH:16]=[CH:17][N:10]4[N:9]=3)=[CH:4][CH:3]=2)[CH:21]=[N:20]1)[CH3:33]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 2-(4-bromo-phenyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (58.0 mg, 0.200 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (45.8 mg, 0.22 mmol) and sodium hydrogen carbonate (20.2 mg, 0.24 mmol) in 0.4 ml DMF and 0.2 ml water is flushed with nitrogen and heated to 40° C. Then bis(triphenylphosphine)-palladium(II)-chloride (2.8 mg, 0.004 mmol) is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 18 hours. The mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off washed with water and dried under vacuum. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to afford 2-[4-(1-ethyl-1H-pyrazol-4-yl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as off-white crystals; HPLC/MS 1.64 min (C), [M+H] 292;

Workup

customis flushed with nitrogen
temperatureThe reaction mixture is heated to 80° C.
temperatureto cool to room temperature
filtrationThe resulting precipitate is filtered off
washwashed with water
customdried under vacuum
customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent

Sources & evidence

ORD record: ord-4681b69cfe654e3cb0fa5f9a8ce01662
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174995B2

Reaction notes

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