2-Methyl-3-butyn-2-ol → 4-(3-Bromothieno[2,3-c]pyridin-2-yl)-2-methylbut-3-yn-2-ol

HRID 389563Notes

Reaction equation

Br[C:2]1[S:10][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[Br:11].[CH3:12][C:13]([OH:17])([C:15]#[CH:16])[CH3:14].CCN(C(C)C)C(C)C>O1CCOCC1.[Cu]I.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>[Br:11][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:10][C:2]=1[C:16]#[C:15][C:13]([CH3:14])([OH:17])[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 2,3-dibromothieno[2,3-c]pyridine (400 mg, 1.37 mmol), 2-methyl-3-butyn-2-ol (121 μL, 1.24 mmol), copper (I) iodide (24 mg, 0.12 mmol) and DIPEA (2.16 mL, 12.41 mmol) in 1,4-dioxane (16 mL) was added Pd(PPh3)2Cl2 (174 mg, 0.25 mmol). The mixture was evacuated and refilled with nitrogen (3×), then stirred at 50° C. for 2 h. Solvent was evaporated and the resultant mixture was dissolved in EtOAc. The organic solution was washed with water and brine, dried over anhydrous sodium sulfate, and purified by ISCO column chromatography (0 to 5% MeOH:DCM) to afford 319 mg (87%) of the title compound as a light-yellow solid. MS (ESI): 296.38, 298.35 [M+H]+; HPLC tR=0.94 min (HPLC: Analytical—2 min).

Workup

customThe mixture was evacuated
additionrefilled with nitrogen (3×)
customSolvent was evaporated
dissolutionthe resultant mixture was dissolved in EtOAc
washThe organic solution was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
custompurified by ISCO column chromatography (0 to 5% MeOH:DCM)

Sources & evidence

ORD record: ord-99974af5f0bb46b18a072fdf9d645124
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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