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Potassium Carbonate → Methyl 6-chloro-5-(6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl)-1h-indole-3-carboxylate

HRID 1054878
ノート
印刷プレビュー

反応式

HRID 1054878 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[N:6][C:7]=1[O:8][CH3:9].[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][NH:23]2)=[CH:19][C:18]=1B1OCC(C)(C)CO1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][NH:23]2)=[CH:19][C:18]=1[C:2]1[C:7]([O:8][CH3:9])=[N:6][C:5]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 866988541-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol

生成物 1

HCID 86698855Methyl 6-chloro-5-(6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl)-1h-indole-3-carboxylate収率 35.7%

試薬・触媒・溶媒 1

HCID 21863594
Toluene ethanol
溶媒

反応条件

温度
80 °C

実験手順

A vial was charged with 1-(5-bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol (100.0 mg, 0.37 mmol), methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (176.4 mg, 0.55 mmol), Pd(dppf)C12 (26.8 mg, 0.04 mmol), potassium carbonate (152 mg, 1.10 mmol, 2M/L aqueous) and toluene/ethanol (1.5 mL/0.5 mL). The mixture was purged with nitrogen for 5 minutes and then sealed. The reaction was heated to 80° C. overnight. The mixture was cooled to room temperature and filtered. The filtrate was diluted with water (5 mL) and extracted with ethyl acetate (5 mL×3). The organic layer was dried (sodium sulfate) and concentrated. The resulting residue was purified through prep. TLC (petroleum ether: ethyl acetate, 2:1) to give the title compound (52.5 mg, 35.7%) as an off-white solid. 1H NMR (400 MHz, CDCl3) ppm: 8.62 (br. s), 8.05 (s, 1H), 7.89 (d, 1H), 7.50 (s, 1H), 7.35 (d, 1H), 6.00 (d, 1H), 4.61 (m, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.73-3.57 (m, 4H), 2.24-2.05 (m, 2H).

後処理

  1. customThe mixture was purged with nitrogen for 5 minutes
  2. customsealed
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered
  5. additionThe filtrate was diluted with water (5 mL)
  6. extractionextracted with ethyl acetate (5 mL×3)
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe resulting residue was purified through prep

出典と根拠

ORDレコード
ord-a63f07bdef3e4964adb17487a29c3214
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394285B2

反応ノート

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