1,2-Dimethoxyethane → 2-[3-Methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7751

Reaction equation

HRID 7751 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].[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[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][C:22]1[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Product 1

HCID 102366482-[3-Methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (190 mg, 0.58 mmol), 3-pyridylboronic acid (70 mg, 0.58 mmol), Pd(Ph3P)4 (70 mg, 0.06 mmol), K2CO3 (200 mg, 1.5 mmol), DME (6 mL) and H2O (3 mL) was degassed with bubbling Ar for 15 min. The mixture was heated at 80° C. for 1 h. The reaction was poured into H2O (40 mL) and extracted with CH2Cl2 (2×30 mL). The organic extracts were dried (MgSO4) and concentrated to afford a colorless solid. Purification of the solid by flash chromatography on silica gel (EtOAc:hexanes 3:1) afforded the desired 2-[3-methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.56 (br s, 1H), 8.45 (br d, 1H), 7.74–7.80 (m, 3H), 7.50–7.58 (m, 2H), 7.32–7.37 (m, 2H), 7.17–7.24 (m, 2H), 4.00 (s, 2H), 3.93 (s, 3H). MS (ESI) 317 (M+H)+.

Workup

  1. customwas degassed with bubbling Ar for 15 min
  2. additionThe reaction was poured into H2O (40 mL)
  3. extractionextracted with CH2Cl2 (2×30 mL)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford a colorless solid
  7. customPurification of the solid by flash chromatography on silica gel (EtOAc:hexanes 3:1)

Sources & evidence

ORD record
ord-a07ed9330a9844e9a2231169eeda2c61
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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