Sodium Bicarbonate → HCID 90408880, compound

HRID 871087Notes

Reaction equation

HRID 871087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9](I)=[CH:10][C:3]=12.CC1(C)C(C)(C)OB([C:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH:31]=2)O1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9]([C:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH:31]=3)=[CH:10][C:3]=12

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 224772394-Chloro-2-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90408880HCID 90408880, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (7.50 g, 17.33 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (6.43 g, 20.80 mmol), tetrakis(triphenylphospine)palladium (0.801 g, 0.693 mmol) and aqueous sodium bicarbonate (40 mL) in N,N-dimethylformamide (160 mL) was flushed with nitrogen and heated at 85° C. for 24 hours. The mixture was diluted with water and brine and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography on silica (ISCO Companion), eluting with a gradient of 8:2 to 7:3 heptanes/ethyl acetate to give the title compound. MS (ESI+) m/z 488.0 (M+H)+.

Workup

  1. customwas flushed with nitrogen
  2. additionThe mixture was diluted with water and brine
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica (ISCO Companion)
  9. washeluting with a gradient of 8:2 to 7:3 heptanes/ethyl acetate

Sources & evidence

ORD record
ord-7b3850977a3748acbba99546336d497e
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

Loading…