Diisopropylethylamine → HCID 67362777, compound

HRID 271685Notes

Reaction equation

HRID 271685 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-7a5a26f340964bbcb7ec7659f4f91906
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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