Cesium carbonate → 5-(4-Chloro-phenyl)-4-(4-hydroxymethyl-phenyl)-2-methyl-1-(4-sulfamoyl-phenyl)-1h-pyrrole-3-carboxylic acid ethyl ester

HRID 1913398

反応式

HRID 1913398 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10](I)=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)[C:7]=1[CH3:29])=[O:5])[CH3:2].[OH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(O)C.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:35]2[CH:36]=[CH:37][C:32]([CH2:31][OH:30])=[CH:33][CH:34]=2)=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)[C:7]=1[CH3:29])=[O:5])[CH3:2]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 248942295-(4-Chloro-phenyl)-4-iodo-2-methyl-1-(4-sulfamoyl-phenyl)-1h-pyrrole-3-carboxylic acid ethyl ester

生成物 1

HCID 248942275-(4-Chloro-phenyl)-4-(4-hydroxymethyl-phenyl)-2-methyl-1-(4-sulfamoyl-phenyl)-1h-pyrrole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
110 °C

実験手順

To a mixture of Example 96 (33 mg, 0.060 mmol), 4-(hydroxymethyl)phenylboronic acid (12 mg, 0.080 mmol), palladium acetate (2.2 mg, 0.010 mmol) suspended in ethanol (0.50 mL) was added 1 M aqueous Cs2CO3 (0.080 mL, 0.080 mmol), and heated in a microwave (Personal Chemistry: Emrys Creator) at 110° C. for 15 minutes. The mixture was diluted with Et2O (2 mL), stirred thoroughly, filtered through diatomaceous earth with Et2O rinse. The filtrate was washed with 1 M pH 7 potassium phosphate buffer, dried (Na2SO4), filtered and concentrated under reduced pressure and the residue chromatographed on an Alltech silica column (average pore size 60 Å, particle size 50 μM) (30→10% hexanes/Et2O) to provide a white foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.81 (d, 2H), 7.49 (d, 2H), 7.48 (bs, 2H), 7.14 (d, 2H), 7.14 (d, 2H), 7.06 (d, 2H), 6.95 (d, 2H), 5.10 (t, 1H), 4.45 (d, 2H), 4.02 (q, 2H), 2.32 (s, 3H), 1.0 (t, 3H); MS (ESI) m/z m/z 525/527.

後処理

  1. filtrationfiltered through diatomaceous earth with Et2O
  2. washrinse
  3. washThe filtrate was washed with 1 M pH 7 potassium phosphate buffer
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue chromatographed on an Alltech silica column (average pore size 60 Å, particle size 50 μM) (30→10% hexanes/Et2O)
  8. customto provide a white foam

出典と根拠

ORDレコード
ord-58cbdab785cb4441977a94aee962b8f5
出典データセット
uspto-grants-2013_12
特許番号
US08609713B2

関連ノート

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