Triethylamine → 1-Benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642413노트

반응식

HRID 642413 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 684277721-Benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 684273231-Benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester수율 93.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (500 mg, 1.68 mmol), pivaloyl chloride (0.250 mL, 2.02 mmol), 4-dimethylaminopyridine (21 mg, 0.168 mmol) and triethyl amine (0.468 mL, 3.36 mmol) in dichloromethane (5 mL) was stirred at room temperature for 1 h; then the reaction mixture was diluted with EtOAc, washed with saturated NaCl solution and subsequently the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified with column to give the desired product as a clear oil (599 mg, 93%). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.62 (s, 1H), 7.31-7.20 (m, 6H), 6.53-6.51 (m, 1H), 5.40 (s, 2H), 4.41 (q, 2H, J=7.3 Hz), 1.47 (s, 9H), 1.41 (t, 3H, J=7.3 Hz).

후처리

  1. washwashed with saturated NaCl solution
  2. dry with materialsubsequently the organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified with column

출처 및 근거

ORD 기록
ord-c21011174c7e44b4925144cbacb27c14
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

반응 노트

불러오는 중…