Cesium carbonate → 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7741

반응식

HRID 7741 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[O:18][CH3:19].[NH:20]1[CH:24]=[CH:23][N:22]=[N:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:19][O:18][C:4]1[CH:5]=[C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][N:20]1[CH:24]=[CH:23][N:22]=[N:21]1.[CH3:19][O:18][C:4]1[CH:5]=[C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][N:21]1[N:22]=[CH:23][CH:24]=[N:20]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 178418936HCID 178418936, 화합물

생성물 2

HCID 101255962-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazoleHCID 101718252-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A slurry of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1H-1,2,3-triazole (70 mg, 1.0 mmol), and Cs2CO3 (325 mg, 1.0 mmol) and MeCN (10 mL) was stirred vigorously at rt for 8 h. Silica gel (600 mg) was added, and the reaction mixture was concentrated to dryness. The residue was purified by flash chromatography on silica gel (linear gradient of EtOAc in hexanes from 0 to 100% over 25 min) to afford 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole and 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole as colorless solids. 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 7.72–7.78 (m, 3H), 7.69 (s, 1H), 7.59 (s, 1H), 7.53–7.56 (m, 1H), 7.31–7.34 (m, 2H), 7.20 (d, 1H), 5.59 (s, 2H), 3.96 (s, 3H). MS (ESI) 307 (M+H). 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 7.76–7.80 (m, 3H), 7.68 (s, 1H), 7.56–7.59 (m, 2H), 7.34–7.38 (m, 2H), 7.04 (d, 1H), 5.74 (s, 2H), 3.99 (s, 3H). MS (ESI) 307 (M+H)+.

후처리

  1. additionSilica gel (600 mg) was added
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe residue was purified by flash chromatography on silica gel (linear gradient of EtOAc in hexanes from 0 to 100% over 25 min)

출처 및 근거

ORD 기록
ord-d309ba83d2484108a07efc99551b2565
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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