2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 66889350, compound

HRID 1893718Notes

Reaction equation

[Li]CCCC.Br[C:7]1[N:8]=[C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[S:10][CH:11]=1.C(O[B:24]1[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]1)(C)C>CCOCC>[CH3:19][C:15]1[N:14]=[C:13]([O:12][C:9]2[S:10][CH:11]=[C:7]([B:24]3[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]3)[N:8]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

According to Scheme 5, Step 3: At −78° C., under a nitrogen atmosphere, BuLi (3.69 mmol, 1.48 mL) was added dropwise to a solution of 2-(4-bromothiazol-2-yloxy)-6-methylpyridine (1.68 mmol, 455 mg) in Et2O (17 mL). After 5 minutes of stirring at −78° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.69 mmol, 0.75 mL) was added and the resulting mixture was stirred at room temperature for 20 minutes. The reaction was quenched with a NH4Cl saturated aqueous solution and was extracted with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (70:30 to 30:70) as eluent to yield 2-(6-methylpyridin-2-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.49 mmol, 157 mg, 29%).

Workup

stirringthe resulting mixture was stirred at room temperature for 20 minutes
customThe reaction was quenched with a NH4Cl saturated aqueous solution
extractionwas extracted with EtOAc
dry with materialThe combined organic phases were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude mixture was purified by flash chromatography over silica gel

Sources & evidence

ORD record: ord-57d49eb84ed34fcf9c084bee6aebb704
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513252B2

Reaction notes

Loading…