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

HRID 713458

반응식

HRID 713458 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 11194830Cuprous 2-thiophenecarboxylate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5519f890ff84bf9bf6ab184dfd0df64
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181266B2

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