Sodium Bicarbonate → HCID 90411407, compound

HRID 1521953Notes

Reaction equation

HRID 1521953 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:15](I)=[CH:16][C:9]=23)[CH:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH:38]=2)O1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:15]([C:37]4[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH:38]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 90412233HCID 90412233, compound

Product 1

HCID 90411407HCID 90411407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 87B (1.600 g, 3.15 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.071 g, 3.46 mmol), tetrakistriphenylphosphine palladium (0.182 g, 0.157 mmol), and aqueous sodium bicarbonate solution (15 mL) in N,N-dimethylformamide (60 mL) was degassed with nitrogen and heated at 80° C. for 3 hours. After cooling, the mixture was quenched with water and brine and extracted with ethyl acetate (twice). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion flash system eluting with heptane/ethyl acetate (65:35 to 5:5) to afford the title compound. MS (ESI+) m/z 564.1 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was quenched with water and brine
  3. extractionextracted with ethyl acetate (twice)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel using an ISCO Companion flash system
  9. washeluting with heptane/ethyl acetate (65:35 to 5:5)

Sources & evidence

ORD record
ord-dd026b60008f491c92fa87ac702d03e8
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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