Potassium Carbonate → N-isobutyl-2-methyl-2-(4-(1-methyl-1H-pyrrol-2-yl)phenyl)propanamide

HRID 1175609ノート

反応式

HRID 1175609 の反応式
[CH2:1]([NH:5][C:6](=[O:25])[C:7]([CH3:24])([C:9]1[CH:14]=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][CH:10]=1)[CH3:8])[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].[CH3:32][N:33]1[CH:37]=[CH:36][CH:35]=[C:34]1Br>COCCOC.O.[Cl-].[Na+].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>[CH2:1]([NH:5][C:6](=[O:25])[C:7]([CH3:8])([C:9]1[CH:10]=[CH:11][C:12]([C:34]2[N:33]([CH3:32])[CH:37]=[CH:36][CH:35]=2)=[CH:13][CH:14]=1)[CH3:24])[CH:2]([CH3:3])[CH3:4]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 10931723N-methyl-2-bromopyrroleHCID 68776318N-isobutyl-2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanamide

生成物 1

HCID 16005233N-isobutyl-2-methyl-2-(4-(1-methyl-1H-pyrrol-2-yl)phenyl)propanamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
85 °C

実験手順

To a solution of N-isobutyl-2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanamide (example 23a) (19.04 g, 55.14 mmol), K2CO3 (22.86 g, 165.4 mmol), and N-methyl-2-bromopyrrole (7.50 g, 93.74 mmol) in DME/H2O (4/1, 300 mL) was added Pd(PPh3)4 (3.20 g, 2.76 mmol) at RT under argon and the reaction mixture was stirred at 85° C. overnight. After it was cooled down to room temperature, the reaction mixture was diluted with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was purified twice by chromatography on silica gel eluting with EtOAc/Hexanes (1/9) to give the title compound as off-white white solid, which was further purified by recrystallization from hexanes, and dried under vacuum overnight. mp: 59-60° C. 1H NMR (400 MHz, DMSO-d6) δ 7.35 (d, J=7.2 Hz, 2H), 7.31 (d, J=7.2 Hz, 2H), 6.79 (m, 1H), 6.09 (m, 1H), 6.01 (m, 1H), 3.60 (s, 3H), 2.82 (t, J=6.4 Hz, 2H), 1.7 (m, 1H), 1.44 (s, 6H), 0.2 (d, J=7.2 Hz, 6H). MS 299 (MH+).

後処理

  1. temperatureAfter it was cooled down to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe residue was purified twice by chromatography on silica gel eluting with EtOAc/Hexanes (1/9)

出典と根拠

ORDレコード
ord-86a7a39720a14bb3be4294bf0ec477d5
出典データセット
uspto-grants-2010_11
特許番号
US07842324B2

反応ノート

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