Hydrochloric Acid → 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid

HRID 1693707노트

반응식

HRID 1693707 반응식
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[C:9]([C:11]2[C:12]([Cl:28])=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=2)[CH:8]=[N:7][CH:6]=1)C.[OH-].[K+].Cl>C(O)C.O>[Cl:28][C:12]1[C:11]([C:9]2[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=2)[C:4]([OH:29])=[O:3])=[CH:16][N:15]=[C:14]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:13]=12

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 575375885-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid ethyl ester

생성물 1

HCID 575375105-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid수율 111.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매3회

실험 절차

1.070 g (2.48 mmol) of 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid ethyl ester was dissolved in 10 mL of ethanol. 2 mL of 50% w/v solution of potassium hydroxide in water and 10 mL of water were added and the resulting solution was left standing at ambient temperature for 16 h. Subsequently the pH was adjusted to approximately 4 by addition of concentrated aqueous hydrochloric acid and the mixture diluted with 100 mL of water. The resulting precipitate was filtered off and dried by suction to afford 1.1153 g (2.76 mmol, quant.) of 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid. 1H-NMR [500 MHz, d6-DMSO] δ: 9.13 (d, 1H), 8.94 (d, 1H), 8.393 (m, 1H), 8.388 (m, 1H), 7.89 (d, 1H), 6.70 (d, 1H), 5.69 (s, 2H), 3.55 (t, 2H), 0.84 (t, 2H), 0.08 (s, 9H); MS [MH+] m/z: 404; [M−H−] m/z: 402.

후처리

  1. additionwere added
  2. waitthe resulting solution was left
  3. filtrationThe resulting precipitate was filtered off
  4. customdried by suction

출처 및 근거

ORD 기록
ord-0ce091077f764d13adafed0759279513
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158647B2

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