Sodium Carbonate → N-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide

HRID 524375노트

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HRID 524375 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[C:18]1([C:24]([CH3:44])([CH3:43])[C:25]([NH:27]C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CCO>[N:12]1([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([NH:27][C:25](=[O:26])[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:44])[CH3:43])=[CH:3][CH:4]=3)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 533635264-(7-Bromoquinoxalin-2-yl)morpholineHCID 586961232-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide

생성물 1

HCID 67035794N-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide수율 168.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

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온도
120 °C

실험 절차

A mixture of 7-bromo-2-morpholin-4-yl-quinoxaline [intermediate example 2.1] (50 mg), 2-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide (87 mg, 0.24 mmol) and Pd(PPh3)4 in 1:1 Toluene/EtOH (2 mL) was treated with 1M aq. sodium carbonate solution and heated at 120° C. under microwave irradiation for 15 minutes. The reaction was partitioned between EtOAc and water, the phases separated and the organic layer concentrated in vacuo. The reaction was repeated and the combined crude products were purified by trituration with DMSO to give the title compound (108 mg). UPLC-MS: RT=1.36 min; m/z (ES+) 453.27 [MH+]; required MW=452.56.

후처리

  1. customThe reaction was partitioned between EtOAc and water
  2. customthe phases separated
  3. concentrationthe organic layer concentrated in vacuo
  4. customthe combined crude products were purified by trituration with DMSO

출처 및 근거

ORD 기록
ord-d0d57fc8a0b141bc9eefbe50462d506e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340528B2

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