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

HRID 1028967노트

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HRID 1028967 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 962Water용매

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온도
145 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dadcf29bce2b4d44a8e9b291984471e2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735384B2

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