Diisopropylethylamine → HCID 67362777, compound

HRID 1916634Notes

Reaction equation

HRID 1916634 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(C(C)C)C(C)C)C>CN(C=O)C.[Na+].[Cl-].CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:6][CH2:5]2

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2×HCID 34115665-Bromoindoline

Product 1

HCID 67362777HCID 67362777, compound

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere 700 mg (3.46 mmol) 5-bromoindoline are added to a solution of 722 mg (4.16 mmol) N-(2-chloroethyl)-pyrrolidine hydrochloride and 1.19 mL (6.93 mmol) ethyldiisopropylamine in 10 mL DMF. The reaction solution is stirred for 21 h at RT and again combined with N-(2-chloroethyl)-pyrrolidine hydrochloride. The reaction solution is heated to 70° C. and stirred for 4 h at this temperature. The solvent is eliminated i.vac. and the residue taken up in 50 mL semisaturated NaCl solution and 50 mL EtOAc. The aqueous phase is extracted twice with 50 mL DCM, the combined organic extracts are dried over Na2SO4 and the solvent is eliminated i.vac.

Workup

  1. temperatureThe reaction solution is heated to 70° C.
  2. stirringstirred for 4 h at this temperature
  3. extractionThe aqueous phase is extracted twice with 50 mL DCM
  4. dry with materialthe combined organic extracts are dried over Na2SO4

Sources & evidence

ORD record
ord-f5a288807d544d65b40762236179932b
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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