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

HRID 1777582

반응식

HRID 1777582 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Carbon tetrabromide (3.27 g, 9.65 mmol) was added to a solution of triphenylphosphine (2.56 g; 9.65 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 minutes. To this green suspension was added a solution of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2 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 residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane) to give 1.08 g (45%) of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid.

후처리

  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 residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-d610fbfc39a14794985643cf250607fa
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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