3-Chloro-4-methoxybenzeneboronic acid → 4-(3-Chloro-4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butylester

HRID 713458

反応式

HRID 713458 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](SC2C=CC=CC=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1COCC1.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].S1C=CC=C1C([O-])=O.[Cu+]>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](=[O:27])[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 2

HCID 32475223-Chloro-4-methoxybenzeneboronic acidHCID 893758004-Phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 712360784-(3-Chloro-4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butylester収率 88.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 11194830Cuprous 2-thiophenecarboxylate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 3-chloro-4-methoxyphenylboronic acid (0.87 g, 4.67 mmol), ligand TFP (0.14 g, 0.6 mmol), Pd2dba3 (0.29 g, 0.31 mmol), copper (I) thiophene-2-carboxylate (0.89 g, 4.7 mmol) was added a solution of 4-phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 3.1 mmol) in 10 mL of THF while purging with N2 at 50° C. After 18 hours the reaction mixture was diluted with ethyl acetate, filtered through celite then concentrated in vacuo. Purification by flash chromatography gave the title compound (1.02 g, 2.74 mmol). MS (ESI) m/z 354.0 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.42 min.

後処理

  1. customwhile purging with N2 at 50° C
  2. additionAfter 18 hours the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through celite
  4. concentrationthen concentrated in vacuo
  5. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-f5519f890ff84bf9bf6ab184dfd0df64
出典データセット
uspto-grants-2015_11
特許番号
US09181266B2

関連ノート

読み込み中…