Water → 6-({[t-Butyl(dimethyl)silyl]oxy}methyl)nicotinonitrile

HRID 2247743노트

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HRID 2247743 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N:6][CH:7]=1.O.[CH3:18][N:19]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Si:10]([O:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[N:19])=[CH:7][N:6]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

참가 물질

7

반응물 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 116594545-Bromo-2-({[t-butyl(dimethyl)silyl]oxy}methyl)pyridine

생성물 1

HCID 224732046-({[t-Butyl(dimethyl)silyl]oxy}methyl)nicotinonitrile수율 93%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매

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온도
100 °C

실험 절차

A solution of 5-bromo-2-({[t-butyl(dimethyl)silyl]oxy}methyl)pyridine (0.30 g, 1.0 mmol) that was obtained in Example 23 (23a), zinc cyanide (0.18 g, 1.5 mmol), bis(dibenzylideneacetone)palladium (18 mg, 0.02 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (44 mg, 0.08 mmol) in N-methyl-2-pyrrolidinone (4 ml) was stirred at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into water and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (0.23 g) in a yield of 93% as a white crystalline solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ether
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-c563039b8dfd485a8dac4f4967d7e6a6
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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