Sodium Carbonate → HCID 25120563, 화합물

HRID 1640927노트

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HRID 1640927 반응식
[F:1][C:2]1[C:3]([C:16]2[S:20][C:19]3[C:21](B4OC(C)(C)C(C)(C)O4)=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[N:12]2)=[N:6][CH:7]=1.[F:34][C:35]1C2[C:38](=[N:39][CH:40]=CC=2Br)[NH:37][CH:36]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl.[CH3:77][CH:78](O)[CH3:79]>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].O.CC#N.CS(C)=O.C1COCC1.O1CCOCC1.CN(C=O)C>[N:11]1([CH2:10][CH2:9][NH:8][C:5]2[N:4]=[C:3]([C:16]3[S:20][C:19]4[C:21]([C:77]5[C:35]([F:34])=[CH:36][N:37]=[C:38]6[NH:39][CH:40]=[CH:79][C:78]=56)=[CH:22][CH:23]=[CH:24][C:18]=4[CH:17]=3)[C:2]([F:1])=[CH:7][N:6]=2)[CH:15]=[CH:14][N:13]=[N:12]1

참가 물질

15

반응물 7

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 17749109Barium hydroxide, octahydrateHCID 21906603Chloroform isopropyl alcoholHCID 66738069HCID 66738069, 화합물HCID 667381024-Bromo-3-fluoro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 25120563HCID 25120563, 화합물수율 47%

시약·촉매·용매 7

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

Combine {5-fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-yl}-(2-[1,2,3]triazol-1-yl-ethyl)-amine (0.105 g, 0.23 mmol), 3-fluoro-4-bromo-1H-pyrrolo[2,3-b]pyridine (51 mg, 0.30 mmol), barium hydroxide octahydrate (0.21 g, 0.68 mmol, alternatively sodium carbonate, potassium carbonate, sodium bicarbonate), Pd(dppf)Cl2 (20 mg, 0.025 mmol) in 2 mL of mixed solvent of DMF (alternatively dioxane, THF, DMSO, and CH3CN) and water (4/1, v/v). Heat the reaction mixture to 80° C. for 2.5 h. (or microwave heating for 10-60 min). Cool to RT. Dilute it with chloroform/IPA (3:1, v/v) 50 mL. Wash it with water and saturated aqueous sodium chloride and dry over magnesium sulfate. Remove the organic solvent to give the crude product. Purify by column chromatography (hexane to ethyl acetate) to afford the title compound (0.05 g, 47%). MS (ES) m/z 475 [M+1]+.

후처리

  1. temperature(or microwave heating for 10-60 min)
  2. temperatureCool to RT
  3. washWash it with water and saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. customRemove the organic solvent
  6. customto give the crude product
  7. customPurify by column chromatography (hexane to ethyl acetate)

출처 및 근거

ORD 기록
ord-c099a162d9de41d3a4ac2d3f8fcebe00
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114872B2

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