Iodoethane → 2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester

HRID 1517539Notes

Reaction equation

HRID 1517539 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:28][CH3:29])=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:37][CH3:38]>CN(C=O)C>[CH2:37]([O:18][C:17](=[O:19])[C:16]1[CH:20]=[C:21]([O:28][CH3:29])[C:22]([C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:23][C:15]=1[C:14]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:38]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 673744112-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid

Product 1

HCID 673750432-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 1—To a solution of 76 (100 mg, 0.26 mmol) in DMF (3 mL) were added Cs2CO3 (101 mg, 0.31 mmol) and iodoethane (25 μL, 0.31 mmol). The reaction mixture was stirred at RT overnight then quenched with H2O and thrice extracted with EtOAc. The combined organics were washed with H2O (3×), dried (MgSO4), filtered and concentrated under reduced pressure to afford 109 mg (99%) of 2-(2-benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester (78) as a pale yellow foam.

Workup

  1. customthen quenched with H2O and thrice
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with H2O (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39949e6499324b66af7f169f55b6ece4
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

Loading…