Diisopropylethylamine → 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone

HRID 512677Notes

Reaction equation

HRID 512677 reaction equation
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[C:4]([OH:6])=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][NH:31][N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][N:31]([C:4](=[O:6])[CH:3]([O:2][CH3:1])[C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:9][CH:8]=3)[N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acidHCID 178488676HCID 178488676, compound

Product 1

HCID 584320151-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanoneYield 489.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxy-2-(4-morpholinophenyl)acetic acid (0.1 g, 0.42 mmol) and 3-(3,4-dimethoxyphenyl)-1H-pyrazole (0.86 g, 0.42 mmol) in anhydrous DMF (4 mL) at room temperature was added diisopropylethylamine (0.22 ml, 1.26 mmol) then bromotripyrrolidinophosphonium hexafluorophosphate (0.23 g, 0.50 mmol). After 24 hrs, saturated aqueous NaHCO3 was added. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-60% EtOAc-hexanes) gave 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone as a white solid (0.90 g, 50% yield). MS: m/z 438.2 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (0-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-93cc5cea40194411b8ed9061a42c7af0
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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