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

HRID 7741
Notes
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Reaction equation

HRID 7741 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-d309ba83d2484108a07efc99551b2565
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087601B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes