Sodium Carbonate → HCID 25120563、化合物

HRID 1640927ノート

反応式

HRID 1640927 の反応式
[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

参加物

15

反応物 7

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

生成物 1

HCID 25120563HCID 25120563、化合物収率 47%

試薬・触媒・溶媒 7

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-c099a162d9de41d3a4ac2d3f8fcebe00
出典データセット
uspto-grants-2012_02
特許番号
US08114872B2

反応ノート

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