Toluene → HCID 44197809, compound

HRID 1969103Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(B(O)O)CCCCC=1.C(=O)([O-])[O-].[K+].[K+]>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.C(O)C>[C:18]1([C:2]2[CH:3]=[C:4]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-pyridin-2-yl-amine (0.063 g, 0.26 mmol), 2 mL of toluene, 0.5 mL of ethanol, cyclohexen-1-yl boronic acid (0.065 g, 0.51 mmol), Pd(PPh3)4 (0.032 g, 0.027 mmol), and 0.36 mL of a 2 M aq. potassium carbonate solution under N2 was stirred at 170° C. in a microwave for 3 h. The mixture was partitioned between 10 mL of a 10% NaOH solution and 10 mL of dichloromethane. The aqueous layer was further extracted with 10 mL of dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to 0.093 g of a pale yellow oil. Column chromatography (0->33% EtOAc/hexanes) afforded 0.050 g (66%) of (6-cyclohex-1-enyl-imidazo[1,2-b]pyridazin-8-yl)-pyridin-2-yl-amine as a white solid.

Workup

customThe mixture was partitioned between 10 mL of a 10% NaOH solution and 10 mL of dichloromethane
extractionThe aqueous layer was further extracted with 10 mL of dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated to 0.093 g of a pale yellow oil

Sources & evidence

ORD record: ord-2388399d6eab4e20b8836f3f51f182cd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426441B2

Reaction notes

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