Formic Acid → HCID 86686016、化合物

HRID 2277721ノート

反応式

HRID 2277721 の反応式
[N:1]1([C:6](=[O:8])[CH3:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](I)[CH:15]=1.C(N(CC)CC)C.C(O)=O>CN(C=O)C.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.O>[Br:9][C:10]1[CH:15]=[C:14]([CH:3]2[CH2:4][CH2:5][N:1]([C:6](=[O:8])[CH3:7])[CH2:2]2)[CH:13]=[N:12][CH:11]=1

参加物

8

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8204093-Bromo-5-iodopyridineHCID 11446304HCID 11446304、化合物

生成物 1

HCID 86686016HCID 86686016、化合物収率 15%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1-(2,5-dihydro-pyrrol-1-yl)-ethanone (70 mg, 0.63 mmol), 3-bromo-5-iodo-pyridine (283 mg, 1 mmol), triethyl amine (130 mg, 1.26 mmol), formic acid (41 mg, 0.88 mmol) and tetrakis(triphenylphosphine)palladium(0) (72.8 mg, 0.063 mmol) in DMF (3 mL) was stirred for 24 hours at 90° C. under nitrogen. After cooling to room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. After removal of solvents, the residue was purified by flash chromatography to afford the title compound as yellowish oil (25 mg, 15%). MS: 269.1 (M+H+).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customAfter removal of solvents
  5. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d5c47487d45e47ec857c09928f7089f4
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

読み込み中…