Tributylvinyltin → HCID 57917377, compound

HRID 69296Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[C:8]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH2:27]([Sn](CCCC)(CCCC)C=C)[CH2:28]CC>O1CCOCC1.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>[CH3:26][N:24]1[CH:25]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]3[N:16]([C:12]([CH2:11][C:8]4[CH:9]=[CH:10][C:5]5[N:6]([C:2]([CH:27]=[CH2:28])=[CH:3][N:4]=5)[CH:7]=4)=[CH:13][N:14]=3)[N:17]=2)[CH:22]=[N:23]1

Participants

Conditions

Temperature: 150 °C

Procedure

3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 296, 50 mg, 0.122 mmol) was dissolved in dioxane (0.5 mL) in a microwave reactor. Then tributyl(vinyl)tin (36.9 μL, 0.122 mmol) and tetrakis(triphenylphosphine)palladium (1.4 mg, 0.001 mmol) were introduced. The RM was heated at 150° C. for 30 min under microwave irradiations. The solvent was removed and The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and were lyophilized. The residue was dissolved in MeOH and it was passed through an SPE cartridge of HCO3− to remove the TFA salt. The filtrate was evaporated to give the free salt of the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=356).

Workup

customThe solvent was removed
customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
dissolutionThe residue was dissolved in MeOH
customto remove the TFA salt
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-c351297314f447f99107f98170897d16
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822468B2

Reaction notes

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