Formic Acid → HCID 86686016, 화합물

HRID 2277721노트

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HRID 2277721 반응식
[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

참가 물질

8

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8204093-Bromo-5-iodopyridineHCID 11446304HCID 11446304, 화합물

생성물 1

HCID 86686016HCID 86686016, 화합물수율 15%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d5c47487d45e47ec857c09928f7089f4
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133158B2

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