Potassium Phosphate, Tribasic → 6-Cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one

HRID 2069860ノート

反応式

HRID 2069860 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8](=[O:13])[NH:7][CH2:6][CH2:5]2.C1(P([CH:27]2[CH2:32][CH2:31]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH:31]1([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([F:12])[CH:11]=2)[C:8](=[O:13])[NH:7][CH2:6][CH2:5]3)[CH2:32][CH2:27]1

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 594737766-Bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one

生成物 1

HCID 594738126-Cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one収率 697.2%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 6-bromo-8-fluoro-3,4-dihydro-2H-isoquinolin-1-one (1.6 g, 6.5 mmol), tricyclohexylphosphine (0.182 g, 0.65 mmol) and Pd(OAc)2 (0.072 g, 0.032 mmol) in 15 ml toluene placed under argon in a pressure flask was added cyclopropyl boronic acid (1.12 g, 13 mmol), potassium phosphate (6.9 g, 32.5 mmol) and 1.5 ml water. The flask was sealed and the mixture was heated under stirring for 4 hours at 100° C. After cooling the reaction mixture was diluted with ethyl acetate and the organic phase washed with brine, dried with sodium sulfate and concentrated. The residue was purified by flash chromatography (ethyl acetate) affording 0.93 g (71.5% yield) of I.

後処理

  1. customplaced under argon in a pressure flask
  2. customThe flask was sealed
  3. temperaturethe mixture was heated
  4. temperatureAfter cooling the reaction mixture
  5. washthe organic phase washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-ba35b7b5d356428ca7a788f395099874
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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