Water → Isoquinoline-6-carbonitrile

HRID 2079993

반응식

HRID 2079993 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.C(OCC)(=O)C.O.[CH3:19][N:20](C)C=O>[C-]#N.[Zn+2].[C-]#N.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>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([C:19]#[N:20])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 3136816-Bromoisoquinoline

생성물 1

HCID 23130705Isoquinoline-6-carbonitrile수율 83%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매2회

반응 조건

온도
100 °C

실험 절차

Next, to a solution of 6-bromoisoquinoline (382 mg, 1.84 mmol) in N,N-dimethylformamide (3.8 mL) were added zinc cyanide (431 mg, 3.67 mmol) and tetrakis(triphenylphosphine)palladium(0) (42 mg, 0.0367 mmol) under nitrogen atmosphere, and the mixture was stirred at 100° C. for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (42 mg, 0.0367 mmol) was further added, and the mixture was stirred for 2.5 hours at 100° C. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for extraction, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane:ethyl acetate), and isoquinoline-6-carbonitrile (234 mg, 83%) was obtained as a yellow solid.

후처리

  1. stirringthe mixture was stirred for 2.5 hours at 100° C
  2. customwas allowed to room temperature
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-fa825fb8627a471fbee2aa51e35456ec
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

연결된 노트

불러오는 중…