Sodium Bicarbonate → HCID 18359981, compound
Reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[CH:9]=[CH:8][S:7][C:6]=12.O1C=C[CH:12]=[C:11]1P(C1OC=CC=1)C1OC=CC=1.C(C([Sn])=C(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>CN1C(=O)CCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH:11]([C:2]1[N:3]=[CH:4][N:5]2[CH:9]=[CH:8][S:7][C:6]=12)=[CH2:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 5.0 g of 7-iodoimidazo[5,1-b]thiazole in 40 ml of NMP were added under the atmosphere of argon 550 mg of tris(dibenzilideneacetone) dipalladium, 558 mg of tri-2-furyl phosphine, and 6.42 ml of tri-n-butylvinyltin, and the mixture was reacted at 70° C. for 1.5 hours, and at 80° C. for 2 hours. The reaction mixture was poured into a mixture of 50 ml of a saturated aqueous sodium hydrogen carbonate solution and 50 ml of a saturated saline, and extracted two times with 200 ml of ethyl acetate. The organic layers were combined, washed three times with 200 ml of saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=15:1) to give 7-vinylimidazo[5,1-b]thiazole in an amount of 1.99 g.
Workup
- customthe mixture was reacted at 70° C. for 1.5 hours
- extractionextracted two times with 200 ml of ethyl acetate
- washwashed three times with 200 ml of saline
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue thus obtained
- customwas purified by column chromatography on silica gel (dichloromethane:ethyl acetate=15:1)
Sources & evidence
- ORD record
- ord-6e5c53452fec48219009b0c75726e7bb
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310056B1
Reaction notes
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