Bromoacetyl bromide → HCID 46916455, 화합물

HRID 2045933노트

반응식

HRID 2045933 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[Br:18][CH2:19][C:20](Br)=[O:21].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C>[Br:18][CH2:19][C:20]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:21]

참가 물질

6

반응물 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 8072643-(2-Quinoxalinyl)aniline

생성물 1

HCID 46916455HCID 46916455, 화합물수율 22.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (3-quinoxalin-2-ylphenyl)amine (2 g, 9.04 mmol) in THF (50 mL), bromoacetyl bromide (0.83 mL, 9.5 mmol) was added, followed by diisopropylethylamine (DIEA, 1.8 mL, 10.85 mmol), at room temperature. The reaction mixture was stirred at room temperature for 24 hrs, the slurry was diluted with ethyl acetate and the organic phase was washed with water (50 mL). The insoluble solid was filtered and analysed to afford 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (700 mg, 22% yield). The mother liquer was evaporated in vacuo to afford a second batch of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (1.8 g, 58% yield). LCMS calculated for C18H15N3O (M+H): 290.33. found 290.24. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.62 (1H, br.), 9.52 (1H, s), 8.55 (1H, m), 8.12-8.18 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 4.12 (2H, s).

후처리

  1. washthe organic phase was washed with water (50 mL)
  2. filtrationThe insoluble solid was filtered

출처 및 근거

ORD 기록
ord-463ad31e067a4c068767d7b3c58be48b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592415B2

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