(S)-(-)-1-(4-chlorophenyl)ethylamine → HCID 59593296, compound

HRID 1754692Notes

Reaction equation

HRID 1754692 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1>CN1CCCC1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]([NH:27][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]3[C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:11][CH:10]=3)=[CH:6][N:7]=2)[CH3:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 1550852(S)-(-)-1-(4-chlorophenyl)ethylamineHCID 59593271HCID 59593271, compound

Product 1

HCID 59593296HCID 59593296, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(6-bromo-pyridin-3-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (91, 100 mg, 0.0003 mol) and (S)-1-(4-chloro-phenyl)-ethylamine (92, 0.5 g, 0.003 mol) in N-methylpyrrolidine (3 mL) was stirred at 150° C. in microwave for 100 minutes. The reaction mixture was concentrated under vacuum and the residue was purified with silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (P-0075, 0.03 g, 20%). MS (ESI) [M+H+]+=363.18.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified with silica gel column chromatography
  3. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-f239fee9b8924621a295bcbfdf48cfc2
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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