2-(Tributylstannyl)pyridine → 2-(1-(6-methyl-4-oxo-3-(pyridin-2-yl)-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione

HRID 405976Notes

Reaction equation

HRID 405976 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]2[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:14]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26])[CH3:15].C([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:9]1[N:6]2[C:7](=[O:8])[C:2]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[C:3]([CH:14]([N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH3:15])[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 668313402-(1-(3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 668313802-(1-(6-methyl-4-oxo-3-(pyridin-2-yl)-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(1-(3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)-ethyl)isoindoline-1,3-dione (0.9386 g, 2.277 mmol), 2-(tributylstannyl)pyridine (1.098 mL, 3.05 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.263 g, 0.228 mmol) in 1,4-dioxane (18.97 mL) was stirred using an overhead stirrer at 110° C. After 20 h, the mixture was cooled to rt and concd under reduced pressure to give a black liquid. The black liquid was purified by column chromatography on a 80 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane over 25 min and then 100% isocratic of EtOAc for 25 min to give 2-(1-(6-methyl-4-oxo-3-(pyridin-2-yl)-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione as a yellow solid: Mass Spectrum (ESI) m/e=411.1 (M+1).

Workup

  1. customat 110° C
  2. customconcd under reduced pressure to give a black liquid
  3. customThe black liquid was purified by column chromatography on a 80 g of Redi-Sep™ column
  4. customover 25 min

Sources & evidence

ORD record
ord-95020385f6bb48a4b2b66751bf14775b
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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