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

HRID 1470810ノート

反応式

HRID 1470810 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 120 mg of 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 343 m/z (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-82dcddfcc4d34b1ab4169e93d1c19ec3
出典データセット
uspto-grants-2015_04
特許番号
US09006468B2

反応ノート

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