Trityl chloride → HCID 67984870, compound

HRID 530836Notes

Reaction equation

HRID 530836 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[NH:4][N:3]=1.[H-].[Na+].[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[N:4]([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178468688HCID 178468688, compound

Product 1

HCID 67984870HCID 67984870, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-bromo-1H-indazole-5-carboxylate (10.72 gm, 0.04 mol) in 160 mL of THF was added NaH (2.8 g, 0.068 mol) portionwise at 5-10 C under ice/water bath. The solution was stirred for 15 minutes further until no more bubbling. Tritylchloride (14 g, 0.05 mol) was added in several portions. After the addition, the cooling bath was removed and the orange suspension was stirred at room temperature for overnight. The reaction mixture was poured slowly into 100 mL of saturated NH4Cl with stirring and 100 mL EtOAc. The layers were separated and the aqueous phase extracted with Ethyl acetate (2 L×2). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2SO4, filter and concentrated. The solid was triturated with hexane (100 mL), filtered and washed with hexane and dried under vacuum to give 20 gram product as light yellow solid.

Workup

  1. customno more bubbling
  2. additionAfter the addition
  3. customthe cooling bath was removed
  4. stirringthe orange suspension was stirred at room temperature for overnight
  5. additionThe reaction mixture was poured slowly into 100 mL of saturated NH4Cl
  6. stirringwith stirring
  7. customThe layers were separated
  8. extractionthe aqueous phase extracted with Ethyl acetate (2 L×2)
  9. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrated
  13. customThe solid was triturated with hexane (100 mL)
  14. filtrationfiltered
  15. washwashed with hexane
  16. customdried under vacuum

Sources & evidence

ORD record
ord-7b8ddf125196471db000119b2b952816
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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