Benzyl Bromide → HCID 9967388, compound

HRID 1743352Notes

Reaction equation

HRID 1743352 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)=[CH:7][CH:6]=1)=[O:4].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H-].[Na+]>C1COCC1>[CH2:19]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([C:8]2[O:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[N:11]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 9856210HCID 9856210, compound

Product 1

HCID 9967388HCID 9967388, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(5-methoxycarbonyl-2-furyl)-1H-indazole (2.0 g, 8.3 mmol) and benzyl bromide (2.5 mL, 21.0 mmol) in THF (100 mL) was added dropwise via dropping funnel to a suspension of sodium hydride (60% dispersion in oil: 0.50 g, 12.5 mmol) in THF (200 mL). The resultant mixture was stirred at room temperature for 20 h. The mixture was poured onto brine and the layers separated. The aqueous layer was extracted three times with ether and then the combined organic material was washed with saturated aqueous NaHCO3 solution, dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica (EtOAc:cyclohexane 1:4) and then the product was recrystallised (EtOAc/hexane) to give a yellow solid: mp 137–138° C.; MS (EI) M+ 332; 1H-NMR (CDCl3) 3.97 (s, 3H), 5.67 (s, 2H), 7.03 (d, 1H, J=3.7 Hz), 7.22–7.43 (m, 9H), 8.27 (d, 1H, J=8.1 Hz); Anal. (C20H16N2O3) C, calcd 72.28; found 71.92, H, calcd 4.85; found 4.75, N, calcd 8.43; found 8.39.

Workup

  1. additionThe mixture was poured onto brine
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted three times with ether
  4. washthe combined organic material was washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica (EtOAc:cyclohexane 1:4)
  8. customthe product was recrystallised (EtOAc/hexane)
  9. customto give a yellow solid

Sources & evidence

ORD record
ord-2d9d9d5043de456f94d31dd3b40fa97b
Source dataset
uspto-grants-2006_03
Patent number
US07009056B2

Reaction notes

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