Nitrogen → HCID 57445398, compound

HRID 1993364Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([F:16])[CH:9]=2)=[CH:6][CH:7]=1.B1([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)C2CCCC1CCC2.C([O-])([O-])=O.[K+].[K+].N#N>CN(C=O)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:26]([C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([F:16])[CH:9]=2)=[CH:6][CH:7]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 3-chloro-6-(3-fluoro-4-methoxy-phenyl)-pyridazine (Step 1, 2.0 g, 8.38 mmol), B-benzyl-9-BBN (0.5 mL in THF, 20 mL) and K2CO3 (3.5 g, 25.1 mmol) in 30 mL of DMF was degassed with N2 for 5 min. Cat. Pd(DPPF)Cl2 (731 mg, 1 mmol) was then added and the reaction was heated at 65° C. for 3 h (preheated oil bath). The mixture was poured into ice water and extracted with 50 mL 2×EtOAc. The combined organic phases were washed with 50 mL of brine and dried over Na2SO4. The solution was concentrated in vacuo and the crude was purified by silica gel column chromatograph (50% EtOAc/Hexane to EtOAc) to give light yellow solid. MS (ESI pos. ion) m/z: 295.3 (M+H). Calc'd Exact Mass for C18H15FN2O: 294.32.

Workup

extractionextracted with 50 mL 2×EtOAc
washThe combined organic phases were washed with 50 mL of brine
dry with materialdried over Na2SO4
concentrationThe solution was concentrated in vacuo
customthe crude was purified by silica gel column chromatograph (50% EtOAc/Hexane to EtOAc)
customto give light yellow solid

Sources & evidence

ORD record: ord-b95c7908c6174fc394e4e6df1b1d58b7
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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