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

HRID 1890728ノート

反応式

HRID 1890728 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
96 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8c7922761ecc4751a047111aa4a0a512
出典データセット
uspto-grants-2013_08
特許番号
US08507491B2

反応ノート

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