Triacetoxyperiodinane → 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carbaldehyde

HRID 1748819Notes

Reaction equation

HRID 1748819 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:18][OH:19])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:18]=[O:19])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67005456(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol

Product 1

HCID 867241441-(4-fluorophenyl)-6-methyl-1H-indazole-5-carbaldehydeYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol (1.14 g, 4.45 mmol) was dissolved in DCM (46 mL) and treated with Dess-Martin periodinane (1.87 g, 4.45 mmol). The reaction was stirred at ambient temperature for about 1 h and filtered over a plug of SiO2 rinsing with DCM (50 mL). The filtrate was partially concentrated under reduced pressure and then filtered over a second plug of SiO2 rinsing with DCM (40 mL). The filtrate was concentrated under reduced pressure and the crude material was purified by column chromatography (EtOAc/heptane 100:0 to 0:60) to afford 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carbaldehyde (1.09 g, 4.29 mmol, 96%). LC-MS (Table 1, Method g) Rt=2.01 min, m/z 257 (M+H)+. 1H NMR (CDCl3) δ 10.27 (s, 1H), 8.29 (bs, 2H), 7.72-7.63 (m, 2H), 7.45 (s, 1H), 7.32-7.23 (m, 2H), 2.80 (s, 3H).

Workup

  1. filtrationfiltered over a plug of SiO2 rinsing with DCM (50 mL)
  2. concentrationThe filtrate was partially concentrated under reduced pressure
  3. filtrationfiltered over a second plug of SiO2 rinsing with DCM (40 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude material was purified by column chromatography (EtOAc/heptane 100:0 to 0:60)

Sources & evidence

ORD record
ord-8ce348575fc14ace9dafa4e398ab5e06
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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