Dibutyltin dichloride → HCID 59593301, compound

HRID 1952032Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]([CH3:21])[N:15]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>O1CCCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)=[N:15][C:16]=1[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of p-trifluoromethylbenzaldehyde (16, 1.00 g, 5.74 mmol) in tetrahydrofuran (9 mL) was added 2-amino-5-bromo-6-methylpyridine (33, 1.08 g, 5.77 mmol), followed by dibutyltin dichloride (40 mg, 0.13 mmol). The mixture was stirred for 5 minutes at 25° C. and phenylsilane (0.69 g, 6.4 mmol) was added. The reaction was heated at 50° C. overnight, then the solvent was removed at reduced pressure. Ethyl acetate was added to the resulting solid which was washed with saturated sodium carbonate, dried over magnesium sulfate and filtered. Concentration under reduced pressure afforded a light yellow solid (34, 1.7 g, 4.93 mmol). MS (ESI) [M+H+]+=345.1.

Workup

temperatureThe reaction was heated at 50° C. overnight
customthe solvent was removed at reduced pressure
additionEthyl acetate was added to the resulting solid which
washwas washed with saturated sodium carbonate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationConcentration under reduced pressure
customafforded a light yellow solid (34, 1.7 g, 4.93 mmol)

Sources & evidence

ORD record: ord-b925d320ca954c0f87da0e8fa1231749
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404700B2

Reaction notes

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