Hexane → HCID 66761094, compound

HRID 389532Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[S:4][CH:3]=1.[Li]CCCC.CCCCCC.C(O[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1)(C)C>C1COCC1>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:2]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)=[CH:3][S:4][C:5]2=[CH:6][N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of 3-bromo-5-methoxythieno[2,3-c]pyridine (14.7 mg, 0.0602 mmol) in THF (2.5 mL) was added dropwise 1.60 M n-BuLi in hexane (56.4 μL, 0.0903 mmol) in 5 min under an atmosphere of nitrogen. After stirring at −78° C. for 1 h, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18.8 μL, 0.0903 mmol) was added dropwise. The combined mixture was stirred at −78° C. for another 1 h. The temperature was then gradually raised to RT in 40 min. The reaction was then quenched by addition of MeOH (5 mL) and purified by ISCO chromatography (0 to 20% EtOAc:hexane) to afford 6.6 mg (38%) of the title compound as a light yellow solid. 1H NMR (400 MHz, dioxane-d8): δ 8.72 (d, J=1.2 Hz, 1 H), 8.29 (s, 1 H), 7.48 (d, J=0.8 Hz, 1 H), 3.93 (s, 3 H), 1.35 (s, 12 H); MS (ESI): 292.11 [M+H]+; HPLC tR=1.71 min (TOF: polar—3 min).

Workup

stirringThe combined mixture was stirred at −78° C. for another 1 h
temperatureThe temperature was then gradually raised to RT in 40 min
customThe reaction was then quenched by addition of MeOH (5 mL)
custompurified by ISCO chromatography (0 to 20% EtOAc:hexane)

Sources & evidence

ORD record: ord-80c6da4d99f24ce4b77c0d7c27fcb154
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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