Potassium Phosphate, Tribasic → (2-{5-[(5-Cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxopyridin-3-yl}-4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}phenyl)methyl Acetate

HRID 1918870ノート

反応式

HRID 1918870 の反応式
[C:1]([O:4][CH2:5][CH:6]1[C:11]([N:21]2[C:33](=[O:34])[C:32]3[S:31][C:30]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=4[C:24]=3[CH2:23][CH2:22]2)(B2OC(C)(C)C(C)(C)O2)[CH:10]=[C:9]([F:35])[CH:8]=[CH:7]1)(=[O:3])[CH3:2].Br[C:37]1[CH:38]=[C:39]([NH:45][C:46]2[NH:50][N:49]=[C:48]([CH:51]3[CH2:53][CH2:52]3)[CH:47]=2)[C:40](=[O:44])[N:41]([CH3:43])[CH:42]=1.CC(O[Na])=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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>[C:1]([O:4][CH2:5][C:6]1[C:11]([N:21]2[C:33](=[O:34])[C:32]3[S:31][C:30]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=4[C:24]=3[CH2:23][CH2:22]2)=[CH:10][C:9]([F:35])=[CH:8][C:7]=1[C:37]1[CH:38]=[C:39]([NH:45][C:46]2[CH:47]=[C:48]([CH:51]3[CH2:52][CH2:53]3)[NH:49][N:50]=2)[C:40](=[O:44])[N:41]([CH3:43])[CH:42]=1)(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 67016208(4-Fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-methyl acetateHCID 178418247HCID 178418247、化合物HCID 178479983HCID 178479983、化合物

生成物 1

HCID 67016583(2-{5-[(5-Cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxopyridin-3-yl}-4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}phenyl)methyl Acetate収率 52%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

A 25 mL sealed vial was charged with (4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-methyl acetate 212b (580 mg, 1.16 mmol), 136d (300 mg, 0.97 mmol), CH3COONa (160 mg, 1.94 mmol), K3PO4 (410 mg, 1.94 mmol), PdCl2(dppf) (100 mg, 0.12 mmol), CH3CN (12 mL), and H2O (1 mL). The mixture was heated at 110° C. for 2 hours. The reaction mixture was evaporated and the residue was purified by flash column eluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine to give 136e as a black solid (300 mg, 52%).

後処理

  1. customA 25 mL sealed vial
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by flash column
  4. washeluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine

出典と根拠

ORDレコード
ord-b28157cd5905433b87e27defdf7714a1
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

読み込み中…