Potassium Acetate → Cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate

HRID 1028967ノート

反応式

HRID 1028967 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:26])=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13](B2OC(C)(C)C(C)(C)O2)=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.Br[C:28]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:29]=1[C:30]([O:32][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:31].C([O-])(=O)C.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.O>[NH2:26][C:8]1[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:28]3[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:29]=3[C:30]([O:32][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[O:31])[CH:14]=2)[N:9]=1

参加物

8

反応物 4

HCID 517044Potassium AcetateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67325920Cyclopentyl 2-bromo-3-methylbenzoateHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

生成物 1

HCID 53328993Cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
145 °C

実験手順

3-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.15 g, 0.422 mmol, prepared as Example 2, Step 1-2), cyclopentyl 2-bromo-3-methylbenzoate (0.133 g, 0.470 mmol), potassium acetate (0.079 mL, 1.267 mmol), 2-dicyclohexylphosphino-2′,4′,6′,-triisopropylbiphenyl (0.020 g, 0.042 mmol), palladium(II) acetate (4.74 mg, 0.021 mmol), water (0.3 mL) and ethanol (2 mL) were combined in a microwave vial and heated to 145° C. for 30 min. The crude material was partitioned between water (40 mL) and DCM (50 mL). The organic layer was dried on magnesium sulfate, filtered and concentrated. The crude material was purified by silica chromatography (0-10% methanol in DCM gradient) to give cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate. MS (ESI, pos. ion) m/z: 432 (M+1).

後処理

  1. customThe crude material was partitioned between water (40 mL) and DCM (50 mL)
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica chromatography (0-10% methanol in DCM gradient)

出典と根拠

ORDレコード
ord-dadcf29bce2b4d44a8e9b291984471e2
出典データセット
uspto-grants-2014_05
特許番号
US08735384B2

反応ノート

読み込み中…