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

HRID 1517539노트

반응식

HRID 1517539 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39949e6499324b66af7f169f55b6ece4
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232271B2

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