Tetrahydrofuran → HCID 57752668, compound

HRID 226016Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C([Li])(C)(C)C.B(OC)(OC)OC.[CH3:30][CH2:31][CH2:32][CH2:33]CC.[CH2:36]1[CH2:40]O[CH2:38][CH2:37]1>C(OC(=O)C)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:7]3[N:8]([CH3:13])[C:37]4[CH:38]=[C:32]([CH3:33])[C:31]([CH3:30])=[CH:40][C:36]=4[N:15]=3)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 1.00 g (2.91 mmol) of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine in 60 mL of dry THF is cooled to −78° C. 4.12 mL (7.00 mmol) of 1.7M t-butyllithium in hexanes is added and reaction is stirred at −78° C. for 1 h. 0.818 mL (7.30 mmol) of trimethyl borate is added and reaction is followed by MS and TLC (1:1 hexane:ethylacetate) See indication of the title compound by MS. Allow to stir for an additional hour, quench with 1N hydrochloric acid, dilute with ethyl acetate, separate layers, extract aqueous 3×100 mL ethyl acetate, dry (MgSO4), and concentrated. Triturate in hexanes and filter off solid to give the title compound 6.4 g (53%), MS, ES+=262.2 (M+1).

Workup

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Sources & evidence

ORD record: ord-ba7ed749a8bf46428d75b546d8d4f255
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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