Azido(trimethyl)stannane → HCID 178477887, compound

HRID 1497086Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]([C:17]#[N:18])=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[N:25]([Sn](C)(C)C)=[N+:26]=[N-:27]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)[C:6]([C:17]1[NH:27][N:26]=[N:25][N:18]=1)=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6-Chloro-4-phenyl-2-pyrrolidin-1-yl-quinoline-3-carbonitrile (25 mg, 74.9 μmol, Eq: 1.00) and azidotrimethyltin (30.8 mg, 150 μmol, Eq: 2) were dissolved in xylene (1 ml) and the reaction mixture was heated to 120° C. for 40 h. The mixture was allowed to cool to RT and the solid was filtered off, washed with boiling toluene and suspended in water. The pH was adjusted to 1 by addition of 0.1N HCl and the mixture was extracted with ethyl acetate (3×). The combined organic layers were dried with Na2SO4 and evaporated and the remaining residue was purified by column chromatography (silica gel, DCM/MeOH 9:1) to afford the title compound as yellow solid (5.8 mg). MS (ESI): 377.3 (M+H)+.

Workup

temperatureto cool to RT
filtrationthe solid was filtered off
washwashed with boiling toluene
additionThe pH was adjusted to 1 by addition of 0.1N HCl
extractionthe mixture was extracted with ethyl acetate (3×)
dry with materialThe combined organic layers were dried with Na2SO4
customevaporated
customthe remaining residue was purified by column chromatography (silica gel, DCM/MeOH 9:1)

Sources & evidence

ORD record: ord-f63113b10d084bffa7730ac4773e8ba8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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