2-(Tri-n-butylstannyl)oxazole → HCID 57815469, compound

HRID 385682Notes

Reaction equation

HRID 385682 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:39])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]([CH2:28][C:29]3[N:34]=[CH:33][C:32]4[O:35][CH2:36][CH2:37][O:38][C:31]=4[CH:30]=3)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]2)=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:45]1[O:46][CH:47]=[CH:48][N:49]=1)CCC>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:38]1[C:31]2[CH:30]=[C:29]([CH2:28][N:20]([CH:17]3[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:9]4[C:10]5[C:5](=[N:4][CH:3]=[C:2]([C:45]6[O:46][CH:47]=[CH:48][N:49]=6)[CH:11]=5)[CH:6]=[CH:7][C:8]4=[O:39])[CH2:15][CH2:16]3)[C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[N:34]=[CH:33][C:32]=2[O:35][CH2:36][CH2:37]1

Participants

5

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 57815264HCID 57815264, compound

Product 1

HCID 57815469HCID 57815469, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.10 g of tert-butyl (1-(2-(7-bromo-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate in 2 mL of dioxane, 90 mg of 2-tributylstannyloxazole and 17 mg of bis(tri-tert-butylphosphine)palladium(0) were added under a nitrogen atmosphere, and the mixture was heated under reflux while stirring for 6 hours 30 minutes. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=98:2 to 95:5 to obtain 87 mg of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-(1,3-oxazol-2-yl)-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customThe resultant residue was purified by flash silica gel column chromatography
  4. washelution with chloroform

Sources & evidence

ORD record
ord-5511bb0977de46efab9a811e8914f0de
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

Loading…