Sodium Carbonate → 2-(6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

HRID 876447Notes

Reaction equation

HRID 876447 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([O:21][Si](C(C)(C)C)(C)C)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=2)[CH:7]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[C:29]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=5)[N:12]=4)=[N:9][N:10]=3)[CH:7]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 672305262-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline

Product 1

HCID 1363378092-(6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-olYield 37.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

2-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline (0.500 g, 1.10 mmol), phenylboronic acid (0.167 g, 1.37 mmol), Pd(PPh3)4 (0.0634 g, 0.0549 mmol), and 2M aqueous Na2CO3 (2.74 mL, 5.49 mmol) (degassed with nitrogen 30 minutes prior to use) were combined with 7 mL dioxane (degassed with nitrogen 30 minutes prior to use), sonicated, and heated to 110° C. in a reaction block for 18 hours, during which the reaction went dry. The reaction mixture was cooled to ambient temperature, diluted with DMF, and the suspension was vacuum filtered through compressed Celite, rinsed with DMF, and the filtrate was concentrated. The crude material was purified on silica gel (1-20% methanol in dichloromethane gradient) to give the title compound (0.138 g, 0.408 mmol, 37.1% yield) as a brown solid.

Workup

  1. customdegassed with nitrogen 30 minutes
  2. customsonicated
  3. customwent dry
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. additiondiluted with DMF
  6. filtrationfiltered
  7. washrinsed with DMF
  8. concentrationthe filtrate was concentrated
  9. customThe crude material was purified on silica gel (1-20% methanol in dichloromethane gradient)

Sources & evidence

ORD record
ord-0184eca321d04acda39c7eded792873d
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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