Hydrochloric Acid → HCID 57443273、化合物

HRID 2261760ノート

反応式

HRID 2261760 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1B1OC(C)(C)C(C)(C)O1.[CH3:18][O:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27](Br)=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl>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.C(O)C.CN(C=O)C>[CH3:18][O:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27]([C:7]3[CH:6]=[CH:5][C:4]([OH:17])=[CH:3][C:2]=3[CH3:1])=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:21]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11499811Methyl 6-Bromo-1H-Indole-3-CarboxylateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

生成物 1

HCID 57443273HCID 57443273、化合物収率 63%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (213 mg, 0.910 mmol), 6-bromo-1H-indole-3-carboxylic acid methyl ester (193 mg, 0.759 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.046 mmol), DMF (2.7 mL), ethanol (1.34 mL) and 2M aqueous potassium carbonate (1.34 mL) is heated to 100° C. for 60 hours. The reaction is cooled to room temperature, diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated. The residue is purified with flash chromatography eluting with 25 to 40% ethyl acetate/heptane to give the title compound (134 mg, 63%). ES/MS m/e 280.3 (M−1).

後処理

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThe resulting solution is extracted with ethyl acetate
  3. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified with flash chromatography
  6. washeluting with 25 to 40% ethyl acetate/heptane

出典と根拠

ORDレコード
ord-1bece021923b45818a294d1119247698
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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