(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → 4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 713420

반응식

HRID 713420 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](B(O)O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[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]>COCCOC.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]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 2

HCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 893758004-Phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 712269604-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester수율 89.7%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 11194830Cuprous 2-thiophenecarboxylate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of 2,3-dihydro-1-benzofuran-5-ylboronic acid (0.56 g, 1.56 mmol), ligand TFP (0.07 g, 0.3 mmol), Pd2dba3 (0.28 g, 0.30 mmol), copper (I) thiophene-2-carboxylate (0.45 g, 2.4 mmol) was added a solution of 4-phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.6 mmol) in 15 mL of DME 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 (0.5 g, 1.4 mmol, 87% yield). MS (ESI) m/z 331.8 (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 1.54 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-c8f286941442437f9c0c04f92f909969
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181266B2

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