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Dimethylformamide → 2,2,2-trifluoro-N-(6-formylimidazo[1,2-a]pyridin-2-yl)acetamide

HRID 69195
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HRID 69195 반응식
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][N:9]2[CH:15]=1)=[O:4].C([Mg]Cl)(C)C.CN([CH:26]=[O:27])C.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH:26]=[O:27])=[CH:10][N:9]2[CH:15]=1)=[O:4]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 110136782,2,2-trifluoro-N-(6-iodoimidazo[1,2-a]pyridin-2-yl)acetamideHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 120659512,2,2-trifluoro-N-(6-formylimidazo[1,2-a]pyridin-2-yl)acetamide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
3회

반응 조건

온도
-40 °C

실험 절차

2,2,2-Trifluoro-N-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-acetamide (Stage 153.2, 1 g, 2.82 mmol) was dissolved in THF (15 mL) and cooled down to −40° C. under nitrogen atm. iPrMgCl in THF (2 M, 2.8 mL) was added dropwise. After 1 h stirring, cold DMF (0.65 mL, 8.46 mmol) in THF (1 mL) was added and the RM warmed up to −10° C. in 4 h. NH4Cl solution was added and the mixture was extracted 3 times with EtOAc. Combined organic layers were washed with brine and dried on Na2SO4. After evaporation of the solvent the crude was purified by preparative HPLC with acetonitrile/water (with 0.1% TFA) to afford the title compound (tR 0.88 min (conditions 2), (MH+=258).

후처리

  1. temperaturethe RM warmed up to −10° C. in 4 h
  2. extractionthe mixture was extracted 3 times with EtOAc
  3. washCombined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customAfter evaporation of the solvent the crude
  6. customwas purified by preparative HPLC with acetonitrile/water (with 0.1% TFA)

출처 및 근거

ORD 기록
ord-e232d6d6e2ea446ba1e20fb207ed419d
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822468B2

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