Sodium Carbonate → 1H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-

HRID 1918641

반응식

HRID 1918641 반응식
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([Si:12]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:13]#[C:14][CH2:15][CH2:16][OH:17])[CH3:11].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.ClCCl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14]([CH2:15][CH2:16][OH:17])=[C:13]([Si:12]([CH2:20][CH3:21])([CH2:10][CH3:11])[CH2:18][CH3:19])[NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 110760102-Amino-5-chloro-3-iodopyridine

생성물 1

HCID 110560231H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-수율 88%

시약·촉매·용매 2

HCID 178478483HCID 178478483, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5-chloro-3-iodopyridin-2-amine (2 g; 7.86 mmol), 4-(triethylsilyl)but-3-yn-1-ol (4.35 g; 23.58 mmol); (1,1′-bis(diphenylphosphino)ferrocene)-dichloromethane (0.321 g; 0.393 mmol), lithium chloride (0.333 g; 7.86 mmol) and sodium carbonate (1.67 g; 15.72 mmol) in DMF (15 mL) was heated at 100° C. for approximately 20 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was partitioned between brine and ethyl acetate. After separation the organic layer was evaporated and the residue was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane) to give 2.15 g (88%) of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol as a white solid.

후처리

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between brine and ethyl acetate
  4. customAfter separation the organic layer
  5. customwas evaporated
  6. customthe residue was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-4572b156eda04827b10f40a688a9287b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618138B2

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