2-(Tributylstannyl)pyridine → HCID 59864163, compound

HRID 1993581Notes

Reaction equation

HRID 1993581 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6](Br)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC>C1COCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 59864163HCID 59864163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

The title compound Is synthesized via Stille coupling analogously to the procedure of Zhang et al., Synthetic Commun. 31 (8), 1129-1139 (2001) 3-amino-5-bromo-benzotrifluoride (600 mg, 2.44 mmol), 2-tributylstannyl-pyridine (1.0 g, 2.69 mmol), and tetrakistriphenylphosphin palladium (282 mg, 0.245 mmol) dissolved in THF (10 mL) is stirred under Ar at 90° C. for 7 d. After concentrating under reduced pressure, the reaction mixture is flash chromatographed (silica gel, 2.6×46 cm, AcOEt/hexane: 1:2→2:3) to give compound of Stage 146.1 as a yellow oil: M+H=239.1; 1H-NMR (400 MHz, DMSO-d6): 8.64 (d, 5.0 Hz, 1H), 7.82 (m, 2H), 7.54/7.45 (s/s, 1H/1H), 7.36 (m, 1H9, 6.90 (s, 1H), 5.73 (s/broad, 2H); HPLC: 3.49 min (System 1); Rf (hexane/AcOEt=2:1): 1.5.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customchromatographed (silica gel, 2.6×46 cm, AcOEt/hexane: 1:2→2:3)

Sources & evidence

ORD record
ord-17494bb21cdf463ea1cbf12a44756c9e
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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