Dibutyltin dichloride → HCID 59593301, compound

HRID 1754649Notes

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-672b1ed08d5d458aa7f54f94ae3c4b84
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169250B2

Reaction notes

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