Carbon tetrabromide → 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 58653

反応式

HRID 58653 の反応式
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:25][C:26]1[CH:27]=[C:28]2[C:34]([CH2:35]CO)=[C:33]([Si:38]([CH2:43][CH3:44])([CH2:41][CH3:42])[CH2:39][CH3:40])[NH:32][C:29]2=[N:30][CH:31]=1>C1COCC1>[Br:5][CH2:1][CH2:35][C:34]1[C:28]2[C:29](=[N:30][CH:31]=[C:26]([Cl:25])[CH:27]=2)[NH:32][C:33]=1[Si:38]([CH2:39][CH3:40])([CH2:43][CH3:44])[CH2:41][CH3:42]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110560231H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-

生成物 1

HCID 668319713-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Carbon tetrabromide (3.27 g, 9.65 mmol) was added to the solution of triphenylphosphine (2.56 g; 9.65 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 min. To this green suspension was added a solution of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2.00 g; 6.43 mmol) in THF (20 mL) and the resulting reaction mixture was stirred for 20 hours. The precipitate was eliminated by filtration and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography (eluent: 5 to 40% of ethyl acetate in heptanes) to give 1.08 g (45%) of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid.

後処理

  1. customthe resulting reaction mixture
  2. stirringwas stirred for 20 hours
  3. filtrationThe precipitate was eliminated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude material was purified by flash chromatography (eluent: 5 to 40% of ethyl acetate in heptanes)

出典と根拠

ORDレコード
ord-1504e64caf53435b9df18058f9d387df
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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