2-(Tributylstannyl)-1,3-thiazole → 5-Acetyl-1-(3-(2-thiazolyl)phenyl)benzimidazole

HRID 581910Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.[C:19]([C:22]1[CH:37]=[CH:36][C:25]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31](Br)[CH:30]=3)[CH:27]=[N:28][C:24]=2[CH:23]=1)(=[O:21])[CH3:20]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([C:22]1[CH:37]=[CH:36][C:25]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:6]4[S:7][CH:8]=[CH:9][N:10]=4)[CH:30]=3)[CH:27]=[N:28][C:24]=2[CH:23]=1)(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (50) from Example 17 (3.6 g, 9.7 mmol) in dry THF (20 ml) was added 5-acetyl-1-(3-bromophenyl)benzimidazole (52) (1.5 g, 4.8 mmol) and (PPh3)2PdCl2 (340 mg, 0.48 mmol) under argon. The reaction mixture was stirred at 80° C. for 24 hr in a 50 ml sealed tube. After cooling the mixture was concentrated, triturated with water (100 ml) and extracted with CH2Cl2 (200 ml×3). The extract was washed with brine, dried and concentrated under reduced pressure. The residue was washed with ether to afford crystalline (51) (1.5 g, 89%).

Workup

customsealed tube
temperatureAfter cooling the mixture
concentrationwas concentrated
customtriturated with water (100 ml)
extractionextracted with CH2Cl2 (200 ml×3)
washThe extract was washed with brine
customdried
concentrationconcentrated under reduced pressure
washThe residue was washed with ether

Sources & evidence

ORD record: ord-898bba96f50344efbcbbb62af7101d05
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922725

Reaction notes

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