Potassium Carbonate → HCID 86696367, 화합물

HRID 870667노트

반응식

HRID 870667 반응식
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C.O>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:23]3[CH:24]=[CH:25][C:20]([C:18]([O:17][CH3:16])=[O:19])=[CH:21][CH:22]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 866963223-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine

생성물 1

HCID 86696367HCID 86696367, 화합물수율 67.3%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 18373917Acetonitrile--water (1/1)용매

반응 조건

온도
145 °C

실험 절차

To a mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (386 mg, 1.43 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (310 mg, 1.72 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.07 mmol) and potassium carbonate (296 mg, 2.15 mmol) was added 3:1 acetonitrile/water (5 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated. The residue was dissolved in methanol, and then filtered again. The filtration was finally purified by column chromatography on silica gel (50% ethyl acetate in hexane) to afford methyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoate (312 mg, 67% yield) as a yellow solid: 1H NMR (CHLOROFORM-d) δ: 8.22-8.34 (m, 2H), 8.09-8.20 (m, 2H), 7.93 (s, 1H), 7.71 (d, J=9.6 Hz, 1H), 6.51 (d, J=9.6 Hz, 1H), 3.97 (s, 3H), 3.41-3.53 (m, 2H), 1.72 (t, J=7.2 Hz, 2H), 1.50 (dd, J=15.0, 7.5 Hz, 2H), 1.02 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 325.2 [(M+H)+, calcd for C18H21N4O2 325.2].

후처리

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol
  4. filtrationfiltered again
  5. filtrationThe filtration
  6. customwas finally purified by column chromatography on silica gel (50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-ee6592bf9bec41a3a4792d43a46b5901
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

반응 노트

불러오는 중…