Potassium Carbonate → 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide

HRID 877345

반응식

HRID 877345 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[N:6][CH:7]=1.[CH2:28](B(O)O)[CH2:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C@@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[C:5]2[CH:4]=[CH:3][C:2]([CH2:28][CH2:29][CH3:30])=[CH:7][N:6]=2)=[O:21])=[CH:13][CH:14]=1)([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 3510651-Propylboronic acidHCID 67171186N-[(5)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide

생성물 1

HCID 671730222-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide수율 51%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

실험 절차

N-[(S)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide (0.075 g, 0.18 mmol) was mixed with n-propylboronic acid (0.04 g, 0.44 mmol), PdCl2(dppf)2 (0.014 g, 0.019 mmol), Ag2O (0.10 g, 0.44 mmol) and K2CO3 (0.073 g, 0.53 mmol) and degassed. THF (3 mL) was added and the mixture was heated in microwave at 130 C for 30 min. The reaction mixture was diluted with EtOAc and filtered through Celite. The solvent was removed and the residue was purified by reverse HPLC to give 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide (0.035 g, 51%). ES-MS [M+1]+: 430.1. 1H NMR (CDCl3, 400 MHz) δ 1H NMR (CDCl3, 400 MHz) δ 8.29 (d, J=2.0 Hz, 1H), 7.58 (d, J=6.4 Hz, 1H), 7.45 (dd, J=2.4, 8.0 Hz, 1H), 7.40 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.24-7.19 (ABq, 4H), 6.27 (d, J=7.2 Hz, 1H), 3.98 (s, 3H), 3.62 (s, 2H), 2.94-2.85 (m, J=6.8 Hz, 1H), 2.54 (t, J=7.6 Hz, 2 H), 1.66-1.56 (m, 2H), 1.24 (d, J=6.4 Hz, 6H), 0.93 (t, J=7.2 Hz, 3H). HRMS (ES) [M+1]+ calcd for C23H29N5O: 392.2445. Found: 392.2446.

후처리

  1. customdegassed
  2. additionTHF (3 mL) was added
  3. temperaturethe mixture was heated in microwave at 130 C for 30 min
  4. additionThe reaction mixture was diluted with EtOAc
  5. filtrationfiltered through Celite
  6. customThe solvent was removed
  7. customthe residue was purified by reverse HPLC

출처 및 근거

ORD 기록
ord-16f85acb2ad74fb29ac1b1a09f47c603
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987310B2

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