Triphenylphosphine → 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine

HRID 925326Notes

Reaction equation

HRID 925326 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7]=1[Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[Cl:15][C:12]1[CH:13]=[C:14]2[C:6]([CH2:5][CH2:4][NH2:1])=[C:7]([Si:16]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:21][CH3:22])[NH:8][C:9]2=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 866638403-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 668320582-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamineYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.900 g; 2.68 mmol) and triphenylphosphine (1.05 g; 4.02 mmol) in methanol (25 ml) was stirred at 80° C. for 1 hour and was concentrated under reduced pressure. The residue was dissolved in toluene (15 mL). Hydrochloric acid (2 mL) and water 15 mL were added. After two layers' separation, the aqueous solution was extracted 3×15 mL of toluene and was made alkaline by addition of a solution of sodium hydroxide 2N. The formed precipitate was filtered off. The filtrate was extracted with dichloromethane (5×15 mL). Combined dichloromethane extracts were dried over magnesium sulphate and concentrated under reduced pressure to give 0.515 g (62%) of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine as an oily residue.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in toluene (15 mL)
  3. additionHydrochloric acid (2 mL) and water 15 mL were added
  4. customAfter two layers' separation
  5. extractionthe aqueous solution was extracted 3×15 mL of toluene
  6. additionby addition of a solution of sodium hydroxide 2N
  7. filtrationThe formed precipitate was filtered off
  8. extractionThe filtrate was extracted with dichloromethane (5×15 mL)
  9. dry with materialCombined dichloromethane extracts were dried over magnesium sulphate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7129c4ef69e4adbae73b92c0c30547c
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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