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

HRID 56578ノート

反応式

HRID 56578 の反応式
[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]

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acidHCID 178488676HCID 178488676、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-219e88aae5f844f58058f31227914f50
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

反応ノート

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