Diisopropylethylamine → HCID 117732499, compound

HRID 718629Notes

Reaction equation

HRID 718629 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)#[CH:2].Br[C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1.CCN(C(C)C)C(C)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[N:6]([C:17]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[C:3]([C:1]#[C:2][C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:4]=3)[N:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27627562-BromoquinolineHCID 117732501HCID 117732501, compound

Product 1

HCID 117732499HCID 117732499, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of compound 41d (1.4 g, 3.4 mmol) in DMF (5 mL) was treated with 2-bromoquinoline (2.0 g, 9.6 mol), Pd(PPh3)2Cl2 (240 mg, 0.34 mmol), Cut (30 mg, 0.16 mmol) and DIPEA (4.4 g, 34.11 mmol) under N2. The reaction mixture was stirred at rt overnight, and concentrated in vacuo. The residue obtained was purified by flash column chromatography on silica gel (EtOAc:petroleum ether (1:2)) to obtain compound 41e as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C31H34N6O3: 539.3 (M+H). found: 539.4.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas purified by flash column chromatography on silica gel (EtOAc:petroleum ether (1:2))

Sources & evidence

ORD record
ord-422f299173514172a13552483191f660
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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