Sodium Bicarbonate → HCID 131735520, compound

HRID 522211Notes

Reaction equation

HRID 522211 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][C:12]3[C:8]4[C:9](=[N:24][CH:25]=[CH:26][C:7]=4[C:6]=2[CH:27]=1)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=3I.CC1(C)C(C)(C)OB([C:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=2)O1.C(=O)(O)[O-].[Na+]>CN(C)C=O.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][C:12]3[C:8]4[C:9](=[N:24][CH:25]=[CH:26][C:7]=4[C:6]=2[CH:27]=1)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=3[C:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=1

Participants

6

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 131735518HCID 131735518, compound

Product 1

HCID 131735520HCID 131735520, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 14H (200 mg, 0.403 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (137 mg, 0.443 mmol), tetrakis(triphenylphosphine)palladium(0) (23.28 mg, 0.020 mmol), and sodium bicarbonate solution (1.5 mL, 0.403 mmol) in N,N-dimethylformamide (6 mL) was degassed and heated at 80° C. for 5 hours. After cooling, the mixture was filtered, treated 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 using the ISCO Companion flash system eluting with ethyl acetate/heptanes (15:85 to 20:80) to provide the title compound. MS (ESI+) m/z 552.0 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. additiontreated with water and brine
  4. extractionextracted with ethyl acetate (twice)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica using the ISCO Companion flash system
  10. washeluting with ethyl acetate/heptanes (15:85 to 20:80)

Sources & evidence

ORD record
ord-8d153e1efb994b13949955f53a98076d
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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