Trimethyltin chloride → HCID 59305031, compound

HRID 2240250Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10](I)[C:3]=12.C([Li])(C)(C)C.[CH3:27][Sn:28](Cl)([CH3:30])[CH3:29].[F-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:10]([Sn:28]([CH3:30])([CH3:29])[CH3:27])[C:3]=12

Participants

Conditions

Temperature: -78 °C

Procedure

In a Schlenk flask (dried by heating under high vacuum and venting with argon), 1.0 g of 4-chloro-3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (2.31 mmol) is initially charged in anhydrous THF (30 ml) and cooled to −78° C. 2.85 ml of tert-butyllithium (1.7 M in pentane) (4.85 mmol) is then slowly added dropwise, and the mixture is stirred at −78° C. for 30 min. 2.42 ml of a 1 M solution of trimethyltin chloride in THF are then added dropwise, and the mixture is allowed to warm to RT overnight. 10 ml of a saturated potassium fluoride solution are then added, and the organic phase is separated off and extracted once with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solution is concentrated. The product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1).

Workup

temperatureto warm to RT overnight
customthe organic phase is separated off
extractionextracted once with ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
concentrationthe solution is concentrated
customThe product is purified by column chromatography on silica gel (mobile phase: toluene/ethyl acetate 20:1)

Sources & evidence

ORD record: ord-dce448d63f2b4082b095192af23a8491
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723347B2

Reaction notes

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