4-Bromo-2-(tributylstannyl)thiazole → HCID 86700281, compound

HRID 879468Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[Br:30][C:31]1[N:32]=[C:33]([Sn](CCCC)(CCCC)CCCC)[S:34][CH:35]=1>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.[Cu]I.O1CCOCC1>[Br:30][C:31]1[N:32]=[C:33]([C:2]2[S:3][C:4]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=4)=[C:9]([C@H:18]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=3[N:6]=2)[S:34][CH:35]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 5 mL microwave reaction tube, (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (240 mg, 0.5 mmol), 4-bromo-2-(tributylstannyl)thiazole (0.25 mL, 1.5 eq.), Pd(PPh3)4 (84 mg, 15%) and CuI (14 mg, 15%) were charged, then 4 mL dioxane was added. The reaction mixture was purged N2, then heated to 100° C. for 3 hour. LC-MS of reaction crude showed desired product mass. The reaction crude was partitioned using ethyl acetate and brine. The organic layer was concentrated and purified via CombiFlash column (0-50% ethyl acetate/hexane) to give desired product. LCMS-ESI+: calc'd for C25H25BrClN2O3S2: 565.9, found. 567.0 (M+H+).

Workup

customThe reaction mixture was purged N2
customLC-MS of reaction crude

Sources & evidence

ORD record: ord-31630416ecd046bcad3ddbb1556c9988
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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