2-Propanethiol → 4-(isopropylthio)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 2199325Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12.C([O-])([O-])=O.[K+].[K+].[CH3:27][CH:28]([SH:30])[CH3:29]>O1CCOCC1>[CH:28]([S:30][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12)([CH3:29])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (500 mg, 1.61 mmol) in dioxane (5 mL) were added K2CO3 (668 mg, 4.83 mmol) and 2-propanethiol (0.3 mL, 3.22 mmol). The reaction mixture was stirred for overnight for 70° C. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (5% to 20% Ethyl acetate/Hexane) as a solvent to afford title compound (320 mg, 56% yield). MS m/z: [M+1].

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4, celite
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-cd60ebc846a4491c8e38e9f9a14d6408
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09358231B2

Reaction notes

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