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2-(Tributylstannyl)-1,3-thiazole → 3-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-6-thiazol-2-yl-pyridazine

HRID 1244264
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HRID 1244264 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)=[C:4]([CH2:21][CH2:22][CH3:23])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][N:33]=1)CCC>C1(C)C=CC=CC=1.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:20][C:16]1[N:15]=[C:14]([C:10]2[N:9]([CH2:8][C:5]3[N:6]=[N:7][C:2]([C:29]4[S:30][CH:31]=[CH:32][N:33]=4)=[CH:3][C:4]=3[CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][N:11]=2)[CH:19]=[CH:18][CH:17]=1
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참가 물질

5

반응물 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 103820556-Chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-pyridazine

생성물 1

HCID 104298633-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-6-thiazol-2-yl-pyridazine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140
Toluene
용매

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온도
100 °C

실험 절차

A mixture of 6-chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-pyridazine (268 mg, 0.81 mmol), 2-tributylstannanyl-thiazole (453 mg, 1.21 mmol), and Pd(PPh3)4 (0.08 mmol, 93 mg) in toluene (10 mL) is degassed. The mixture is then heated at 100° C. overnight. Saturated KF aqueous solution (8 mL) is added and the mixture is stirred for 15 minutes. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (15 mL), dried (Na2SO4), and evaporated. Preparative TLC (5% methanol in DCM) purification of the residue provides the title product. 1H NMR (CDCl3) 8.14–8.18 (m, 2H), 7.97 (d, 1H0, 7.83 (q, 1H), 7.50 (d, 1H), 7.20 (d, 1H), 7.18 (d, 1H), 6.80 (dd, 1H), 6.28 (s, 2H), 2.80 (t, 2H), 1.62–1.73 (m, 2H), 0.97 (t, 3H).

후처리

  1. customis degassed
  2. additionSaturated KF aqueous solution (8 mL) is added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC (5% methanol in DCM) purification of the residue

출처 및 근거

ORD 기록
ord-7519edfd623d4a2a94ddf779f93d0515
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122546B2

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