N-bromobutanimide → HCID 25147504, 화합물

HRID 2088493노트

반응식

HRID 2088493 반응식
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:9][CH:8]=1)=[O:5].C1C(=O)N(Br)C(=O)C1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C([O-])(O)=O.[Na+]>C1COCC1.C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C=CC=CC=1.CCO>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)=[CH:16][C:17]=2[CH3:18])=[CH:11][CH:12]=1)=[O:5]

참가 물질

10

반응물 4

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 593342782,6-difluoro-N-(4-(3-methylthiophen-2-yl)phenyl)benzamide

생성물 1

HCID 25147504HCID 25147504, 화합물

시약·촉매·용매 5

HCID 178479802HCID 178479802, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,6-difluoro-N-(4-(3-methylthiophen-2-yl)phenyl)benzamide (A, 1.3 mmol) in THF (5 mL) was added NBS (1.5 mmol) and solution was stirred at rt for 2 h. Pyridin-3-ylboronic acid (1.5 mmol), bis(triphenylphosphino)palladium dichloride (0.05 mmol) and NaHCO3 (3 mmol) was added followed by EtOH (2 mL), toluene (5 mL) and water (5 mL). The mixture was heated at 110° C. for 1 h. The organic layer was separated, concentrated and purified by flash chromatography to give 2,6-difluoro-N-(4-(3-methyl-5-(pyridin-3-yl)thiophen-2-yl)phenyl)benzamide (B, 50 mg) as white solids. 1H-NMR (CD3OD) □ 8.8 (br, 1H), 8.4 (m, 1H), 8.0 (m, 1H), 7.7 (m, 2H), 7.4-7.6 (m, 6H), 7.1 (t, 2H, J=8), 2.38 (s, 3H) ppm; ESMS calcd for C23H16F2N2OS: 406.1. Found: 407.2 (M+H+).

후처리

  1. temperatureThe mixture was heated at 110° C. for 1 h
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-b6516c3f00bb45148603722592a807d4
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435996B2

반응 노트

불러오는 중…