Cesium carbonate → 1,1-Dimethylethyl 3',6'-dihydro-5-(2-pyrimidinyl)[2,4'-bipyridine]-1'(2'h)-carboxylate

HRID 1038091Notes

Reaction equation

HRID 1038091 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH:25]=[C:24](B(O)O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH:23]=[C:24]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[CH:6][N:7]=2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21931462(1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acidHCID 534869812-(6-Bromopyridin-3-yl)pyrimidine

Product 1

HCID 589464631,1-Dimethylethyl 3',6'-dihydro-5-(2-pyrimidinyl)[2,4'-bipyridine]-1'(2'h)-carboxylate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Refluxed mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine (1Q) (200 mg, 0.85 mmol), N-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (290 mg, 0.93 mmol); Cesium Carbonate (500 mg, 1.538 mmol); PdCl2dppf (30 mg) in dioxane/H2O (10 ml v/v 4/1) for 4 hours. Cooled reaction, then evaporated solvent. Extracted with EtOAc (200 ml) washed with H2O (50 ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110 mg, 38%) ESMS (MH, 339).

Workup

  1. temperatureRefluxed
  2. temperatureCooled
  3. customreaction
  4. extractionExtracted with EtOAc (200 ml)
  5. washwashed with H2O (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customyielding a solid which
  10. customchromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110 mg, 38%) ESMS (MH, 339)

Sources & evidence

ORD record
ord-0182a585d8d14053b52688b8c9c07cfa
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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