Nitrogen → HCID 57932899, compound

HRID 1432706Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][N:5]2[CH:11]=1.Br[C:13]1[S:17][C:16]([C:18]2[N:22]([CH3:23])[N:21]=[CH:20][N:19]=2)=[CH:15][C:14]=1[Cl:24].C([O-])([O-])=O.[Cs+].[Cs+].N#N.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[Cl:24][C:14]1[CH:15]=[C:16]([C:18]2[N:22]([CH3:23])[N:21]=[CH:20][N:19]=2)[S:17][C:13]=1[C:11]1[N:5]2[N:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]2=[N:3][C:2]=1[CH3:1]

Participants

Conditions

Temperature: 135 °C

Procedure

A solution of 2,6-dimethyl-imidazo[1,2-b]pyridazine (0.32 g, 2.17 mmol), 5-(5-bromo-4-chloro-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (0.72 g, 2.61 mmol), Cs2CO3 (1.49 g, 4.57 mmol) and DMF (6 mL) is de-gassed for 15 minutes with N2. Pd(OAc)2 (0.024 g, 0.11 mmol) and PPh3 (0.057 g, 0.22 mmol) are added and the solution is heated at 135° C. for 4 hours. The solution is diluted with CH2Cl2 (50 mL), washed with sat. NH4Cl (2×50 mL), water (50 mL), filtered and concentrated. The residue is purified by ISCO flash chromatography (30%-100% EtOAc gradient) furnish the title compound (0.29 g, 0.84 mmol, 39%). 1H NMR (CDCl3) δ 2.49 (s, 3H), 2.50 (s, 3H), 4.10 (s, 3H), 6.92 (d, J=9.2 Hz, 1H), 7.44 (s, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.85 (s, 1H). LC/MS (m/z): calcd. for C15H13ClN6S (M+H)+: 345.1; found: 345.2.

Workup

washwashed with sat. NH4Cl (2×50 mL), water (50 mL)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by ISCO flash chromatography (30%-100% EtOAc gradient)

Sources & evidence

ORD record: ord-cf00e59405f049eba7b2e3a652042979
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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