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Cesium carbonate → HCID 178474049、化合物

HRID 537075
ノート
印刷プレビュー

反応式

HRID 537075 の反応式
I[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9](COCC[Si](C)(C)C)[N:8]=1.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[NH:11][CH:10]=[N:9][N:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 27343222-Chlorophenylboronic acidHCID 66749237HCID 66749237、化合物

生成物 1

HCID 178474049HCID 178474049、化合物収率 73%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 962
Water
溶媒
2 回
HCID 312751,4-Dioxane溶媒

実験手順

To a solution of N-{4-[4-iodo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.18 mg, 0.33 mmol) in 1,4-dioxane (3 mL) was added water (0.4 mL), (2-chlorophenyl)boronic acid (0.067 g, 0.43 mmol), tetrakis (triphenylphosphine) palladium(0) (0.038 g, 0.033 mmol) and cesium carbonate (0.32 mg, 0.99 mmol). The reaction mixture was allowed to stir and was subjected to microwave irradiation at 150° C. for 20 min. The mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered and concentrated. The residue was dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). The reaction mixture was allowed to stir at rt overnight and was then concentrated. The residue was purified by column chromatography to give N-{4-[4-(2-chlorophenyl)-5-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (Compound I-39) (0.095 g, 73%). LCMS (FA): m/z=395.6 (M+H).

後処理

  1. customirradiation at 150° C. for 20 min
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM (5 mL) and to this solution
  7. additionwas added TFA (2 mL)
  8. stirringto stir at rt overnight
  9. concentrationwas then concentrated
  10. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-6057c4d7114a43efb7cbb4678a33f2bd
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859768B2

反応ノート

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