Sodium Carbonate → 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole

HRID 1842045Notes

Reaction equation

HRID 1842045 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[N:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[N+:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[N:3]=[C:2]2[C:36]1[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 589464433-bromo-5-nitro-1-trityl-1H-indazole

Product 1

HCID 601460255-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazoleYield 92.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromo-5-nitro-1-trityl-1H-indazole (1 g, 0.002 mol) was added to a vial containing pyridin-4-ylboronic acid (0.279 g, 0.00227 mol) and tetrakis(triphenylphosphine)-palladium (0.1155 g, 0.0001 mol). After purging the vial with nitrogen gas, dioxane (6 L) and 2M sodium carbonate (0.006 mol) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for 16 h. Upon completion, the mixture was concentrated under vacuo. Water (3 mL) was added and was extracted using dichloromethane (3×3 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using flash chromatography (1:1 Hexane:Ethyl Acetate). Pure product (0.8954 g, 92.8% yield) was recovered.

Workup

  1. additionwas added to the vial respectively
  2. concentrationUpon completion, the mixture was concentrated under vacuo
  3. additionWater (3 mL) was added
  4. extractionwas extracted
  5. customdried
  6. filtrationThe resulting suspension was filtered
  7. concentrationconcentrated
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-23c9c5957b764d64b5e167a8540f6bf8
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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