Dibutyltin dichloride → HCID 59593301, compound

HRID 1367284Notes

Reaction equation

HRID 1367284 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

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 1706782-Pyridinamine, 5-bromo-6-methyl-

Product 1

HCID 59593301HCID 59593301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-708fba5903684c6cb8ffa0a72464901a
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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