Potassium Carbonate → HCID 178502373、化合物

HRID 1411359ノート

反応式

HRID 1411359 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:42])[NH:10][C@H:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]1[NH:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)[N:26]=1)=[O:16])[CH:12]([CH3:14])[CH3:13].[NH2:43][C:44]1[C:45]([Cl:55])=[CH:46][C:47](Br)=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1>C1(C)C=CC=CC=1.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>[CH3:7][O:8][C:9](=[O:42])[NH:10][C@H:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]1[NH:23][CH:24]=[C:25]([C:27]2[CH:28]=[CH:29][C:30]([C:47]3[CH:46]=[C:45]([Cl:55])[C:44]([NH2:43])=[CH:49][C:48]=3[C:50]([F:52])([F:53])[F:51])=[CH:31][CH:32]=2)[N:26]=1)=[O:16])[CH:12]([CH3:14])[CH3:13]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 140993984-Bromo-2-chloro-5-(trifluoromethyl)anilineHCID 178502353HCID 178502353、化合物

生成物 1

HCID 178502373HCID 178502373、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Potassium carbonate (280 mg, 2.0 mmol) was added to a solution of [(S)-2-methyl-1-((S)-2-{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester (200 mg, 0.40 mmol) and 5-amino-2-bromo-4-chlorobenzotrifluoride (110 mg, 0.40 mmol; Preparation 51) dissolved in toluene (1.3 mL) and water (0.43 mL). The reaction mixture was sparged under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (56 mg, 0.48 mmol) was added and the reaction mixture was sparged with nitrogen and heated at 100° C. for 4 h. The reaction mixture was diluted in ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to produce a red solid, which was purified by silica gel chromatography (0-100% ethyl acetate:hexanes) to produce the desired product as a yellow solid.

後処理

  1. customThe reaction mixture was sparged under nitrogen
  2. customthe reaction mixture was sparged with nitrogen
  3. additionThe reaction mixture was diluted in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto produce a red solid, which
  9. customwas purified by silica gel chromatography (0-100% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-4611ca0f847142d2b8a2d8920cd41a7e
出典データセット
uspto-grants-2014_12
特許番号
US08921372B2

反応ノート

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