2-(Methylthio)-4-(tributylstannyl)pyrimidine → 5-Bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1529326노트

반응식

HRID 1529326 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2I.[CH3:18][S:19][C:20]1[N:25]=[C:24]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH:22][N:21]=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.[Cu]I.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:22]1[CH:23]=[CH:24][N:25]=[C:20]([S:19][CH3:18])[N:21]=1

참가 물질

6

반응물 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 679597555-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

생성물 1

HCID 679597215-Bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole수율 42.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A glass microwave reaction vessel was charged with 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (2.04 g, 5.01 mmol), Pd(PPh3)4 (0.555 g, 0.480 mmol), CuI (0.130 g, 0.683 mmol) and 2-(methylthio)-4-(tributylstannyl)pyrimidine (2.23 g, 5.37 mmol, Frontier Scientific). DMF (6 mL) was added and the reaction mixture was sealed under argon and heated thermally at 100° C. for 6.5 h. The solvent was removed in vacuo and the residue was dissolved in MeOH, evaporated onto silica gel and purified by flash chromatography (Isco, (80 gram)) eluting with 2M NH3 in MeOH:DCM (0:1→1:19) to give 855 mg of a tan amorphous solid. m/z: 405.0 [M+1].

후처리

  1. customA glass microwave reaction vessel
  2. customthe reaction mixture was sealed under argon
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in MeOH
  5. customevaporated onto silica gel
  6. custompurified by flash chromatography (Isco, (80 gram))
  7. washeluting with 2M NH3 in MeOH:DCM (0:1→1:19)

출처 및 근거

ORD 기록
ord-007ea0459bfa49a09fbb377175217bc1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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