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

HRID 1693707ノート

反応式

HRID 1693707 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒3 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0ce091077f764d13adafed0759279513
出典データセット
uspto-grants-2012_04
特許番号
US08158647B2

反応ノート

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