Tributylvinyltin → 3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)-6-vinylimidazo[1,2-b]pyridazine

HRID 456175노트

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HRID 456175 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][C:20]=3[F:21])[N:17]([CH3:22])[N:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>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>[F:21][C:20]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH3:22])=[CH:13][C:12]=1[CH2:11][C:8]1[N:6]2[N:7]=[C:2]([CH:23]=[CH2:24])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

참가 물질

4

반응물 2

HCID 81998TributylvinyltinHCID 581906096-Chloro-3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine

생성물 1

HCID 669271833-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)-6-vinylimidazo[1,2-b]pyridazine수율 43.1%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
120 °C

실험 절차

To a degassed solution of 6-chloro-3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine (400 mg, 1.267 mmol), was added Pd(Ph3P)4 (220 mg, 0.190 mmol) and tributyl(vinyl)stannane (422 mg, 1.330 mmol). The reaction mixture was heated to 120° C. for overnight. Then the reaction was quenched with NH4Cl(aq), extracted with DCM, dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with gradient Hex:EA to give 3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)-6-vinylimidazo[1,2-b]pyridazine (168 mg, 43%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.09 (d, 1H), 7.97 (s, 1H), 7.63 (d, 1H), 7.55 (d, 1H), 7.54 (d, 1H), 7.50 (s, 1H), 6.84 (dd, 1H), 6.31 (d, 1H), 5.72 (d, 1H), 4.37 (s, 2H), 3.98 (s, 3H). LCMS (method B): [MH]+=308, tR=2.49 min.

후처리

  1. customThen the reaction was quenched with NH4Cl(aq)
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography with gradient Hex

출처 및 근거

ORD 기록
ord-2471fbbd49ac472d84645c019f88a9e9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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