Diisopropylethylamine → 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine

HRID 1893716노트

반응식

HRID 1893716 반응식
Br[C:2]1[N:3]=[C:4]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[CH3:14][O:15][C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]2[CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=[N:22]2)=[CH:18][CH:17]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1.O.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]>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH:25]=[C:24]([C:2]3[N:3]=[C:4]([O:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[S:5][CH:6]=3)[CH:23]=[N:22]2)=[CH:35][CH:36]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 668718162-(4-Bromothiazol-2-yloxy)pyridine

생성물 1

HCID 668891372-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine수율 14.7%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
150 °C

실험 절차

According to Scheme 3, Step 3: A mixture of 2-(4-bromothiazol-2-yloxy)pyridine (1.56 mmol, 400 mg), 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.87 mmol, 587 mg), PdCl2(dppf) (0.16 mmol, 127 mg) and N-ethyl-N-isopropylpropan-2-amine (3.11 mmol, 0.53 mL) in dioxane/water (1:1, 10 mL) was stirred at 150° C. for 1 hour under microwave conditions. The reaction mixture was filtered through a pad of celite and was washed with DCM. The organic phase was washed with water, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (90:10 to 70:30) as eluent to yield 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine (0.23 mmol, 83 mg, 9%) as an oil.

후처리

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwas washed with DCM
  3. washThe organic phase was washed with water
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude mixture was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-9aa6d61415754e028475a30de29149ec
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513252B2

반응 노트

불러오는 중…