Potassium Carbonate → 4-[4-[4-(Trifluoromethoxy)phenyl]-2-pyridinyl]benzaldehyde

HRID 1189511ノート

反応式

HRID 1189511 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=C(I)C=CN=1.[CH:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:16][C:15]([F:18])([F:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([CH:27]=[O:28])=[CH:30][CH:31]=3)[CH:7]=2)=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 15165112-Chloro-4-iodopyridineHCID 115871572-Chloro-4-[4-(trifluoromethoxy)phenyl]pyridine

生成物 1

HCID 578244174-[4-[4-(Trifluoromethoxy)phenyl]-2-pyridinyl]benzaldehyde収率 63.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

2-Chloro-4-(4-trifluoromethoxyphenyl)-pyridine (0.55 mmol) starting from 2-chloro-4-iodopyridine, 4-formylphenyl boronic acid (0.82 mmol), tetrakis(triphenylphosphine)palladium(0) (0.005 mmol), 2 M potassium carbonate (0.55 mL) and dioxane (3 mL) were combined in a vial and irradiated by microwave for 15 min at 150° C. The reaction mixture was taken up in EtOAc and washed with brine. The organic layer was dried over magnesium sulfate, was filtered and the solvent removed in vacuo. Purification by silica gel chromatography (EtOAc/hexanes) yielded the product (120 mg) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 10.11 (s, 1H), 8.81 (d, J=4.8 Hz, 1H), 8.24 (d, J=8.7 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 7.96 (m, 1H), 7.73 (d, J=9.0 Hz, 2H), 7.49 (dd, J=5.3, 1.8 Hz, 1H), 7.37 (d, J=8.1 Hz, 2H); EIMS m/z 343 (M+).

後処理

  1. customirradiated by microwave for 15 min at 150° C
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationwas filtered
  5. customthe solvent removed in vacuo
  6. customPurification by silica gel chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-7c87d055e95b4e06a593c7da22b7572c
出典データセット
uspto-grants-2014_03
特許番号
US08674109B2

反応ノート

読み込み中…