Hydrochloric Acid → HCID 67981017, compound

HRID 1520021Notes

Reaction equation

HRID 1520021 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=[O:20])=[CH:16][CH:17]=2)[C:12]([Br:21])=[N:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>CN(C=O)C>[Br:21][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=2)[N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86699009HCID 86699009, compound

Product 1

HCID 67981017HCID 67981017, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium borohydride (395 mg; 10.4 mmol; 2.9 eq.) was added in one portion to a solution of tert-butyl-3-bromo-5-formyl-1H-indazole-1-carboxylate (1.20 g; 3.58 mmol; 1.0 eq.) in DMF (30 mL). The reaction mixture was stirred for 3 h then poured into HCl (0.1N solution) and extracted with EtOAc. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the tittle compound as a yellow solid (1.19 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ 8.05 (d, J=8.7 Hz, 1H), 7.69-7.60 (m, 2H), 4.66 (s, 2H), 1.65 (s, 9H). HPLC (Condition A): Rt 3.65 min (purity 81.6%). MS (ESI+): 327.1, 329.1.

Workup

  1. extractionextracted with EtOAc
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-02bdd6235baf4124976a4bd7aab97ec7
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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