2-(Tributylstannyl)pyridine → HCID 66633726, compound

HRID 409030Notes

Reaction equation

HRID 409030 reaction equation
CCCC[Sn]([C:14]1[N:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(CCCC)CCCC.Cl[C:21]1[N:26]=[C:25]2[S:27][C:28]([CH3:30])=[CH:29][C:24]2=[CH:23][C:22]=1[C@@H:31]([N:33]1[C:41](=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]1=[O:43])[CH3:32]>O1CCOCC1.C(OCC)(=O)C>[CH3:30][C:28]1[S:27][C:25]2=[N:26][C:21]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:19]=3)=[C:22]([C@@H:31]([N:33]3[C:34](=[O:43])[C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:41]3=[O:42])[CH3:32])[CH:23]=[C:24]2[CH:29]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 86680504HCID 86680504, compound

Product 1

HCID 66633726HCID 66633726, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a reaction vessel was combined 2-(1,1,1-tributylstannyl)pyridine (0.124 ml, 0.370 mmol), tetrakis triphenylphosphine(0) (35.6 mg, 0.031 mmol), (S)-2-(1-(6-chloro-2-methylthieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (110 mg, 0.308 mmol) in dioxane (3 mL). The reaction was heated to 100° C. for 2 d, cooled to rt, and diluted with ethyl acetate. The organic phase was washed with NaHCO3 and brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography afforded (S)-2-(1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. 1H NMR (400 MHz, CDCl3) δ 8.64 (ddd, J=4.7, 1.8, 0.8 Hz, 1H), 7.72 (td J=7.8, 2.0 Hz, 1H), 7.67 (m, 3H), 7.62 (m, 2H), 7.29 (ddd, J=7.4, 4.9, 1.6 Hz, 1H), 6.98 (q, J=1.4 Hz, 1H), 6.30 (q, J=7.0 Hz, 1H), 2.60 (d, J=1.2 Hz, 3H), 1.97 (d, J=7.2 Hz, 3H) ppm.

Workup

  1. customIn a reaction vessel was combined
  2. temperaturecooled to rt
  3. washThe organic phase was washed with NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-1b9e3e9f24b84c909a91004a87b62f5e
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

Loading…