Cyclopropanemethanol → 3-(Cyclopropylmethoxy)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-5-carbaldehyde

HRID 1038388Notes

Reaction equation

HRID 1038388 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[CH:24]1([CH2:27][OH:28])[CH2:26][CH2:25]1>C(O)C>[CH:24]1([CH2:27][O:28][C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([CH:2]=[O:3])[CH:7]=3)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[N:10]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 584076045-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

Product 1

HCID 584076073-(Cyclopropylmethoxy)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in close analogy to the procedure described in Example 11A using 166 mg (0.372 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole (Example 6A) and 4 ml cyclopropylmethanol (instead of ethanol). The reaction mixture was filtered, and the filtrate was purified by preparative RP-HPLC (acetonitrile/water+0.05% TFA gradient) to afford 53 mg (57% of th.) of the title compound.

Workup

  1. customThe title compound was prepared in close analogy to the procedure
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was purified by preparative RP-HPLC (acetonitrile/water+0.05% TFA gradient)

Sources & evidence

ORD record
ord-eeb6d94702bb4642a3a8fd35416a9565
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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