Sodium Carbonate → HCID 86701172, compound

HRID 572131Notes

Reaction equation

HRID 572131 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][C:17]1[C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][CH:20]=[CH:19][N:18]=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC>[F:14][C:6]1[C:5]([CH3:15])=[C:4]2[C:9]([CH:10]=[C:11]([CH:12]=[O:13])[C:2]([C:22]3[C:17]([CH3:16])=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:3]2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 164142712-Methylpyridine-3-boronic acid, pinacol esterHCID 866626352-Chloro-7-fluoro-8-methylquinoline-3-carbaldehyde

Product 1

HCID 86701172HCID 86701172, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (8.0 g, 35.77 mmol), 2-methylpyridin-3-ylboronic acid pinacol ester (9.58 g, 39.35 mmol), tetrakis-(triphenylphosphine)palladium(0) (207 mg, 18 mmol) and Na2CO3 (5.69 g, 53.66 mmol) in water (50 mL) and DME (100 mL) was degassed and flushed three times with nitrogen gas, then heated at 90° C. for 24 h. The mixture was allowed to cool to room temperature. The reaction mixture was diluted with DCM (150 mL) and washed with water (150 mL). The aqueous phase was extracted with DCM (2×100 mL) and the combined organic fractions were washed with brine (150 mL), then dried (phase separator) and evaporated in vacuo. The crude material was triturated in hexane (50 mL), then the solid was filtered off and dried under vacuum to give the title compound (9.07 g, 90%) as a pale yellow solid. δH (DMSO-d6) 9.94 (s, 1H), 9.09 (1H, s), 8.61 (dd, J 4.9, 1.7 Hz, 1H), 8.26 (dd, J 8.9, 6.4 Hz, 1H), 7.78 (dd, J 7.7, 1.7 Hz, 1H), 7.69 (t, J 9.2 Hz, 1H), 7.40 (dd, J 7.7, 4.9 Hz, 1H), 2.61 (d, J 2.4 Hz, 3H), 2.34 (s, 3H). LCMS (ES+) 281 (M+H)+, RT 2.26 minutes.

Workup

  1. customwas degassed
  2. customflushed three times with nitrogen gas
  3. temperatureto cool to room temperature
  4. additionThe reaction mixture was diluted with DCM (150 mL)
  5. washwashed with water (150 mL)
  6. extractionThe aqueous phase was extracted with DCM (2×100 mL)
  7. washthe combined organic fractions were washed with brine (150 mL)
  8. customdried (phase separator)
  9. customevaporated in vacuo
  10. customThe crude material was triturated in hexane (50 mL)
  11. filtrationthe solid was filtered off
  12. customdried under vacuum

Sources & evidence

ORD record
ord-8b7d7dbbce83457599be21a4b42dfc91
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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