1,2-Dichloroethane → HCID 50919245, compound

HRID 1851892Notes

Reaction equation

HRID 1851892 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([NH2:33])[CH3:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:33][C@H:31]([C:28]4[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=4)[CH3:32])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16212176(1S)-1-(4-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)HCID 63749115HCID 63749115, compound

Product 1

HCID 50919245HCID 50919245, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromobenzyl)-1H-indole-5-carboxylic acid (1.03 g, 3.1 mmol, 1 equiv) in DMF (30 mL) were added the (S)-1-(4-nitrophenyl)ethanamine hydrochloride (695 mg, 3.4 mmol, 1.1 equiv), DIEA (600 μL, 3.4 mmol, 1.1 equiv), HOBt (525 mg, 3.4 mmol, 1.1 equiv) and EDC (658 mg, 3.4 mmol, 1.1 equiv). After stirring 4 h at room temperature, the mixture was diluted with AcOEt and washed with a 0.5 N HCl aqueous solution, a saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. The crude was purified by flash chromatography (Hexane/AcOEt 1/1) to afford a yellow powder (1.3 g, 2.7 mmol, 87%). ESI-MS (m/z): 478/480 [M+H]+.

Workup

  1. washwashed with a 0.5 N HCl aqueous solution
  2. dry with materiala saturated NaHCO3 solution and brine, dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by flash chromatography (Hexane/AcOEt 1/1)

Sources & evidence

ORD record
ord-13a79cfb971c46cd98f9d6ea70905d84
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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