Potassium Phosphate, Tribasic → (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone

HRID 1028955

反応式

HRID 1028955 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9].[O:16]1[CH2:21][CH2:20][N:19]([C:22]2[C:23]([NH2:41])=[N:24][C:25]3[C:30]([CH:31]=2)=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=3)[CH2:18][CH2:17]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.O.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.C(Cl)(Cl)Cl.[Pd].[Pd]>[NH2:41][C:23]1[C:22]([N:19]2[CH2:20][CH2:21][O:16][CH2:17][CH2:18]2)=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]([CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])[CH:29]=2)[N:24]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 63936269(2-Bromophenyl)(tetrahydro-2H-pyran-4-yl)methanoneHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

生成物 1

HCID 53328643(2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone

試薬・触媒・溶媒 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

(2-Bromophenyl)(tetrahydro-2H-pyran-4-yl)methanone (0.46 g, 1.69 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.50 g, 1.13 mmol, prepared as in Example 2, Step 1-2), potassium phosphate tribasic (0.37 mL, 4.50 mmol), 2-dicyclohexylphosphino-2′,4′,6′,-triisopropylbiphenyl (0.054 g, 0.113 mmol), and tris(dibenzylideneacetone)dipalladium (0) chloroform adduct (0.029 g, 0.028 mmol) were suspended in a mixture of dioxane (3 mL) and water (0.5 mL) and heated in the microwave to 120° C. for 30 min. The crude material was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated, dried with magnesium sulfate and evaporated to dryness under reduced pressure before purification using silica column chromatography (0-5% MeOH in DCM). The isolated material was further purified using silica column chromatography (60-100% ethyl acetate in hexane) to give (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone. MS (ESI, pos. ion) m/z: 418 (M+1).

後処理

  1. customThe crude material was partitioned between water (100 mL) and ethyl acetate (200 mL)
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure before purification
  5. customThe isolated material was further purified

出典と根拠

ORDレコード
ord-1f21f75672b84a459e7fa0f278e92218
出典データセット
uspto-grants-2014_05
特許番号
US08735384B2

関連ノート

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