Dimethylformamide → 2-{3-[2-(3-Cyanophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

HRID 1168454Notes

Reaction equation

HRID 1168454 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:34][N:35](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:34]([C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)#[N:35]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 224936532-{3-(2-(3-Bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic acid

Product 1

HCID 224936902-{3-[2-(3-Cyanophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

13 mg of 2-{3-[2-(3-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic acid and 25 mg of zinc cyanide were dissolved in 5 ml of dimethylformamide. The reaction mixture was degassed and charged with argon, and 20 mg of tetrakistriphenylphosphinepalladium were added. The mixture was stirred at 100° C. for 12 hours. After cooling to room temperature, water was added to the reaction mixture, which was then extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, the solvents were removed under reduced pressure and the residue was purified by RP-HPLC. This gave 68 as an amorphous light-yellow solid. C27H28N2O5 (460.53), MS(ESI): 461.20 (M+H+).

Workup

  1. customThe reaction mixture was degassed
  2. additioncharged with argon, and 20 mg of tetrakistriphenylphosphinepalladium
  3. additionwere added
  4. temperatureAfter cooling to room temperature
  5. additionwater was added to the reaction mixture, which
  6. extractionwas then extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. customthe solvents were removed under reduced pressure
  9. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-5a278800554141c4a2e5ada83e3441ae
Source dataset
uspto-grants-2003_09
Patent number
US06624185B2

Reaction notes

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