Diisopropylethylamine → HCID 57800233, compound

HRID 2102093Notes

Reaction equation

HRID 2102093 reaction equation
[C:1]([C:3]1[C:4]([C:21]([F:24])([F:23])[F:22])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12]/[C:13](=[N:16]/[H])/[NH:14][OH:15])[C:7]([CH2:18][CH2:19][CH3:20])=[CH:6]2)#[N:2].[F:25][C:26]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:27]=1[C:28](Cl)=O.C(N(CC)C(C)C)(C)C>C(#N)C>[F:25][C:26]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:27]=1[C:28]1[O:15][N:14]=[C:13]([CH2:12][N:8]2[C:9]3[C:5](=[C:4]([C:21]([F:24])([F:23])[F:22])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[CH2:18][CH2:19][CH3:20])[N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5880822,5-Difluorobenzoyl chlorideHCID 178506477HCID 178506477, compound

Product 1

HCID 57800233HCID 57800233, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (1Z)-2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (0.050 g, 0.154 mmol) in anhydrous acetonitrile (2.0 mL) under N2, was added 2,5-difluorobenzoyl chloride (0.121 g, 0.177 mmol) and N,N-diisopropylethylamine (0.50 mL, 5.21 mmol). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.029 g (42% yield) of pure product: MS (ES) m/z 446 (M+).

Workup

  1. temperatureUpon cooling
  2. additionthe mixture was poured onto a biotage prepak column
  3. customthe mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-76899dd669c54055ad2f3d945c999b73
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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