3-Chloro-6-methylpyridazine → 2-(6-Methylpyridazin-3-ylamino)dibenzothiophene

HRID 2055321Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.Cl[C:16]1[N:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][C:19]1[N:18]=[N:17][C:16]([NH:1][C:2]2[CH:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-aminodibenzothiophene (0.90 g, 4.52 mM), 3-chloro-6-methyl-pyridazine (0.58 g, 4.52 mM), sodium t-butoxide (0.61 g, 6.33 mM), tris(dibenzylidene-acetone)dipalladium(0) (0.083 g, 0.09 mM) and S-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.113 g, 0.18 mM) in toluene (23 ml) was heated to 80° C. for 18 hours under an inert atmosphere. On cooling to room temperature the mixture was diluted with DCM, washed with aqueous potassium carbonate, dried over sodium sulphate and concentrated. Chromatography (eluent gradient of DCM to EtOAc then MeOH:EtOAc (1:9)) gave the product as an off white solid (0.456 g). NMR: 9.38 (brs, 1H), 8.81 (brs, 1H), 8.18 (m, 1H), 8.01 (m, 1H), 7.94 (d, 1H), 7.75 (dd, 1H), 7.50 (m, 1H), 7.36 (d, 1H), 7.14 (d, 1H), 2.50 (s, 3H); m/z 292.29.

Workup

temperatureOn cooling to room temperature the mixture
washwashed with aqueous potassium carbonate
dry with materialdried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-07f89de757e44486ba1ff1a6a607d09c
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332492B2

Reaction notes

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