Methyl p-toluenesulfonate → HCID 86762621, compound

HRID 2409057Notes

Reaction equation

[CH3:1][Si:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[CH:12][N:13]=[CH:14][C:15]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:10]2[CH:9]=[CH:8]1.[H-].[Na+].[CH3:29]C1C=CC(S(OC)(=O)=O)=CC=1>C1COCC1>[CH3:29][N:17]([CH2:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:25])[CH3:26])[CH:8]=[CH:9][C:10]=12)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methylcarbamate (300 mg, 0.796 mmol) in anhydrous THF (30 mL) at 0° C. was slowly added NaH (60% in mineral oil, 48 mg, 1.194 mmol) and stirred at 0° C. for 30 min. To the mixture was added methyl 4-methylbenzenesulfonate (178 mg, 0.955 mmol) followed by stirring at RT for 18 h. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (2:1) to afford 232 mg (74.6%) of tert-butyl methyl((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)carbamate as a yellow solid. MS (ESI): m/z=392.2 [M+1]+.

Workup

customat 0° C.
stirringby stirring at RT for 18 h
customThe reaction mixture was quenched with water (100 mL)
extractionextracted with EtOAc (50 mL×3)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by SiO2 chromatography
washeluting with petroleum ether:EtOAc (2:1)

Sources & evidence

ORD record: ord-2d419fbcbe6b4be9b2a6749f2b9a01ad
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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