Potassium Phosphate, Tribasic → HCID 72206279、化合物

HRID 2204361ノート

反応式

HRID 2204361 の反応式
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:11]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[CH3:21])[C:12](=[O:13])[C:4]=2[CH:3]=1.[C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:40][CH3:41])=[C:35](B(O)O)[CH:36]=1)#[N:30].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1.O>O.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>[Cl:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:21])=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:33]4[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=4[O:40][CH3:41])[C:29]#[N:30])[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]=3[CH:10]2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:19]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 218864351,4-Dioxane--water (1/1)HCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one2 回

生成物 1

HCID 72206279HCID 72206279、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A degassed mixture of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate B) (0.337 mmol), 5-cyano-2-methoxyphenylboronic acid [612833-37-1] (0.675 mmol), Pd(PPh3)4 (0.067 mmol) and K3PO4 (1.350 mmol) in 2:1 dioxane/H2O (4.5 mL) was heated at 100° C. for 4 h. After cooling to rt, the reaction mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic phases were dried (Na2SO4) and concentrated. The residue was dissolved in CH2Cl2 and filtered through a PL-thiol MP SPE cartridge (StratoSpheres), washing through with additional CH2Cl2. The filtrate was re-concentrated and the residue purified using a RediSep® silica gel column to afford the title compound as a yellow solid. tR: 5.43 min (HPLC 1); ESI-MS: tR=1.37 min, [M+H]+ 530/532/534 (LC-MS 1); TLC: Rf=0.29 (1:1 EtOAc/heptanes); 1H-NMR (d6-DMSO, 600 MHz): 8.15 (br s, 1H), 7.95 (m, 1H), 7.77 (m, 2H), 7.37 (m, 2H), 7.31 (d, 1H), 7.24 (m, 1H), 7.15 (m, 1H), 7.10 (m, 1H), 6.51 (s, 1H), 6.31 (s, 1H), 3.85 (m, 1H), 3.85 (s, 3H), 1.91 (s, 3H), 1.29 (m, 3H), 0.46 (m, 3H).

後処理

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. filtrationfiltered through a PL-thiol MP SPE cartridge (StratoSpheres)
  7. washwashing through with additional CH2Cl2
  8. concentrationThe filtrate was re-concentrated
  9. customthe residue purified

出典と根拠

ORDレコード
ord-f2e400552f2246b4ba1617e21d7d39c9
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

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