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Water → 3-Chloro-5-fluoromethoxy-pyridine-2-carbonitrile

HRID 1752499
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HRID 1752499 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH2:10][F:11])=[CH:4][N:3]=1.O.[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].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>[Cl:8][C:7]1[C:2]([C:13]#[N:14])=[N:3][CH:4]=[C:5]([O:9][CH2:10][F:11])[CH:6]=1
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참가 물질

7

반응물 3

HCID 962WaterHCID 6228DimethylformamideHCID 86689169HCID 86689169, 화합물

생성물 1

HCID 666658643-Chloro-5-fluoromethoxy-pyridine-2-carbonitrile

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매
HCID 178418397
HCID 178418397, 화합물
촉매

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온도
145 °C

실험 절차

To a solution of 2,3-dichloro-5-fluoromethoxy-pyridine (1.18 g, 6.02 mmol) in dry DMF (14.00 ml) were added Zinc cyanide (0.341 g, 2.90 mmol) and Zinc powder (3.94 mg, 0.060 mmol). The suspension was flushed with Argon (3×). Then tetrakis(triphenylphosphine)palladium(0) (0.570 g, 0.494 mmol) was added. The reaction was heated to 145° C. for 2 h. Water was added and the aqueous layer was extracted twice with Et2O. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3) to provide the title compound as yellow oil (515 mg).

후처리

  1. customThe suspension was flushed with Argon (3×)
  2. extractionthe aqueous layer was extracted twice with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-38ed1b3761594f80b7f77fc4c44e2dc5
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163011B2

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