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

HRID 1918644Notes

Reaction equation

HRID 1918644 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

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 separation of the two layers, the aqueous solution was extracted with 3×15 mL of toluene and was made alkaline by addition of a solution of sodium hydroxide 2N. The formed precipitate for filtered off. The filtrate was extracted with dichloromethane (5×15 mL). Combined dichloromethane extracts were dried over magnesium sulphate and was 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 separation of the two layers
  5. extractionthe aqueous solution was extracted with 3×15 mL of toluene
  6. additionby addition of a solution of sodium hydroxide 2N
  7. filtrationThe formed precipitate for filtered off
  8. extractionThe filtrate was extracted with dichloromethane (5×15 mL)
  9. dry with materialCombined dichloromethane extracts were dried over magnesium sulphate
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6430994792240d09a535bd8557cb63d
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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