Dimethylformamide → HCID 22480050, compound

HRID 1349672Notes

Reaction equation

HRID 1349672 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:37][CH:38]([CH3:40])[CH3:39]>CCOC(C)=O>[CH3:37][CH:38]([CH3:40])[CH2:39][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropane2×HCID 11430Potassium Carbonate2×HCID 136379272HCID 136379272, compound

Product 1

HCID 22480050HCID 22480050, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-hydroxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (219 mg, 0.686 mmol), potassium carbonate (K2CO3, 568 mg, 4.12 mmol, 6.00 equiv.), 2.00 mL of dimethylformamide (DMF), and 1-bromo-2-methylpropane (Aldrich, 300 mg, 2.18 mmol, 3.20 equiv.) were stirred at room temperature for 2 h, and then heated at 40° C. for 22 h. Additional potassium carbonate (568 mg, 4.12 mmol, 6.00 equiv.), and 1-bromo-2-methylpropane (Aldrich, 300 mg, 2.18 mmol, 3.20 equiv.) were added, and heating continued for another 28 h. The mixture was diluted with EtOAc, washed with 2×sat. aq. NaHCO3, 2×sat. aq. NaCl, and dried (Na2SO4). Purification by silica gel chromatography using 20% EtOAc in hexanes afforded the title compound (190 mg, 73.6% yield): ES-MS (m/z) 376 [M+1]+.

Workup

  1. temperatureheated at 40° C. for 22 h
  2. temperatureheating
  3. waitcontinued for another 28 h
  4. washwashed with 2×
  5. dry with materialaq. NaCl, and dried (Na2SO4)
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-16c3905dd50d4d6d8cdbdfddcdb79f47
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…