3-Bromo-2-methyl-thieno[3,2-b]pyridine → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[3,2-b]pyridin-3-yl)-imidazo[1,2-b]pyridazine

HRID 226065노트

반응식

HRID 226065 반응식
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[CH3:11].[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24](I)=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]>C1COCC1.[Zn]>[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24]([C:2]3[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[S:4][C:3]=3[CH3:11])=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]

참가 물질

5

반응물 2

HCID 577526323-Bromo-2-methyl-thieno[3,2-b]pyridineHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

생성물 1

HCID 577526838-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[3,2-b]pyridin-3-yl)-imidazo[1,2-b]pyridazine수율 9.2%

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

380 mg of 3-Bromo-2-methyl-thieno[3,2-b]pyridine (1.66 mmol) is placed into the vial with 3.56 ml of Reiki Zn, suspension in THF (2.50 mmol) and capped and heated at 100C for 2 h. The excess Zinc is allowed to settle down and the solution is transferred to the vial containing 250 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.72 mmol) and 48 mg of PdCl2(pddf) (0.06 mmol) in 2 ml of dry THF. The vial is capped by Teflon cap and heated at 80C for overnight. The reaction mixture is quenched by sat.NH4Claq. and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt: 2 M NH3 in MeOH=20:4:1) to give 24.2 mg of the title compound. Yield 9.2%. mass spectrum (m/e): 365 (M+1); 1H-NMR (CDCl3): 8.66 (dd, 1H, J=4.7 Hz, 1.4 Hz), 8.16 (dd, 1H, J=8.1 Hz, 1.4 Hz), 7.25 (dd, 1H, J=8.1 Hz, 4.7 Hz), 6.68 (s, 1H), 3.43 (m, 1H), 2.50 (s, 3H), 2.47 (s, 3H), 2.46 (s, 3H), 1.88 (m, 4H), 0.93 (m, 6H) ppm.

후처리

  1. customcapped
  2. customcap
  3. customThe reaction mixture is quenched by sat.NH4Claq
  4. extractionand extracted by CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-a5fc92c4d80f4a38af5b6e6f045d67e9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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