Sodium Bicarbonate → HCID 18359981, compound

HRID 382599Notes

Reaction equation

HRID 382599 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

7

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

  1. customthe mixture was reacted at 70° C. for 1.5 hours
  2. extractionextracted two times with 200 ml of ethyl acetate
  3. washwashed three times with 200 ml of saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. 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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