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Potassium Phosphate, Tribasic → 2-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-5-isobutyl-1,3,4-oxadiazole

HRID 634219
ノート
印刷プレビュー

反応式

HRID 634219 の反応式
[CH2:1]([C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)[CH:2]([CH3:4])[CH3:3].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:73]1[N:78]=[C:77]([CH:79]2[CH2:81][CH2:80]2)[CH:76]=[CH:75][N:74]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:79]1([C:77]2[CH:76]=[CH:75][N:74]=[C:73]([C:13]3[C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:7]5[O:6][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[N:9][N:8]=5)[CH:11]=4)[N:15]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:14]=3)[N:78]=2)[CH2:81][CH2:80]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 49758247HCID 49758247、化合物HCID 683281102-isobutyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole

生成物 1

HCID 683284252-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-5-isobutyl-1,3,4-oxadiazole
収率 40%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
130 °C

実験手順

To a 20 mL microwave vial was added 2-isobutyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (233 mg, 0.530 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15.2 mg, 0.032 mmol), Pd2(dba)3 (14.6 mg, 0.016 mmol), 2-bromo-4-cyclopropylpyrimidine (CombiPhos Catalysts Inc., 121 mg, 0.610 mmol) and potassium phosphate (338 mg, 1.59 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and water (0.4 mL) and heated in the microwave at 130° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification (eluting with 10-60% EtOAc in Hex) afforded 2-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-5-isobutyl-1,3,4-oxadiazole (108 mg, 40%) as a light yellow viscous oil. MS (ESI, pos. ion) m/z: 514.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 9.27 (1H, s), 8.50-8.58 (2H, m), 8.09-8.13 (2H, m), 7.86 (2H, d, J=8.4 Hz), 7.24 (2H, s), 7.07 (1H, d, J=5.1 Hz), 2.84 (2H, d, J=7.2 Hz), 2.35 (3H, s), 2.29 (1H, s), 1.91 (1H, br. s.), 1.34-1.40 (2H, m), 1.17 (2H, dd, J=7.8, 2.9 Hz), 1.07 (6H, d, J=6.7 Hz).

後処理

  1. customby purging with argon
  2. additionThe solids were treated with dioxane (4.0 mL) and water (0.4 mL)
  3. additionThe mixture was treated with H2O
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification (eluting with 10-60% EtOAc in Hex)

出典と根拠

ORDレコード
ord-2e58bccb659842bea6787d367b5a9b0b
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321756B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート