Potassium Phosphate, Tribasic → 3,4-dihydroisoquinolin-1(2H)-one

HRID 1890728노트

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HRID 1890728 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6](C[C@H]1COC(C)(C)O1)[C:7]2=[O:12].ClC1C=CC(N)=CC=1C1NC(C2C=CC=CC=2)=CN=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:7]1(=[O:12])[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][NH:6]1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 498408204-Chloro-3-(5-phenyl-1H-imidazol-2-yl) anilineHCID 58317912(S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one

생성물 1

HCID 1508963,4-dihydroisoquinolin-1(2H)-one

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
96 °C

실험 절차

To a round-bottom flask under argon containing (S)-5-bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one (227 mg, 0.79 mmol), 4-chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline (213 mg, 0.79 mmol), Pd2(dba)3 (143 mg, 0.158 mmol), xantphos (260 mg, 0.316 mmol), potassium phosphate (505 mg, 2.37 mmol) is added anhydrous dioxane (1.6 ml). The mixture is stirred at 96° C. for 18 hours, cooled to room temperature, filtered through a celite pad and washed with THF. The crude product is purified by flash column chromatography using 1% methanol in dichloromethane as eluent to give S)-5-(4-Chloro-3-(5-phenyl-1H-imidazol-2-yl)phenylamino)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one as a dark brown solid. LC-MS m/z: 530.1 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washwashed with THF
  4. customThe crude product is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-8c7922761ecc4751a047111aa4a0a512
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507491B2

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