Dichloromethane → 3-Fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde

HRID 1897611ノート

反応式

HRID 1897611 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[O:13][CH2:12]3)O1.Br[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([F:29])[C:26]=1[CH:27]=[O:28].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.C(OCC)(=O)C>[F:29][C:25]1[CH:24]=[N:23][CH:22]=[C:21]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[O:13][CH2:12]3)[C:26]=1[CH:27]=[O:28]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 534291923-Bromo-5-fluoropyridine-4-carboxaldehydeHCID 580746235-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-2-benzofuran-1-one

生成物 1

HCID 866748373-Fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (210 mg, 0.809 mmol) in DMF (4 mL) was added 3-bromo-5-fluoro-pyridine-4-carbaldehyde (150 mg, 0.735 mmol) and 2M aqueous sodium carbonate (0.735 mL, 1.471 mmol). The reaction mixture was flushed and evacuated with N2 twice followed by the addition of PdCl2(dppf).CH2Cl2 adduct (30.0 mg, 0.037 mmol). The reaction mixture was stirred at 100° C. for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with water twice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford 3-fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde, which was taken into the next step without further purification.

後処理

  1. customThe reaction mixture was flushed
  2. customevacuated with N2
  3. additiontwice followed by the addition of PdCl2(dppf)
  4. temperatureThe reaction was cooled to room temperature
  5. washwashed with water twice
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5bc6b573d38847b48c32628213cb1ff0
出典データセット
uspto-grants-2013_08
特許番号
US08519134B2

反応ノート

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