Sodium Bicarbonate → HCID 90412055, compound

HRID 1521997Notes

Reaction equation

HRID 1521997 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:10](I)=[CH:11][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.O.[Cl-].[Na+].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>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:10]([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:11][C:3]=12

Participants

7

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 904139044-Chloro-5-fluoro-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90412055HCID 90412055, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 23713072Sodium chloride dihydrateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 231B (6.70 g, 15.34 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (4.89 g, 15.81 mmol), tetrakis(triphenylphosphine)palladium (0.532 g, 0.460 mmol), and sodium bicarbonate solution (40 mL, 15.34 mmol) in N,N-dimethylformamide (160 mL) was degassed and heated at 80° C. overnight. The mixture was diluted with water/brine and extracted with ethyl acetate (twice). The combined organic layers were washed with water, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (8:2 to 7:3) to give the title compound. MS (ESI+) m/z 492.0 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (twice)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel using an ISCO Companion
  7. washeluting with heptanes/ethyl acetate (8:2 to 7:3)

Sources & evidence

ORD record
ord-783e8ec877474ea7a8caf65c5ef5d1ef
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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