Diisopropylethylamine → HCID 18617738, compound

HRID 1264212Notes

Reaction equation

HRID 1264212 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]#[N:14].[CH:15](N(CC)C(C)C)([CH3:17])[CH3:16].[C:24](=O)([O-:38])[O:25]N1C2C=CC=C(CC=C)C=2N=N1>C(Cl)Cl.C1COCC1>[C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([CH2:3][CH2:2][NH:1][C:24]([O:38][CH2:16][CH:15]=[CH2:17])=[O:25])[CH:5]=2)[NH:9][CH:8]=1)#[N:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11217658HCID 11217658, compoundHCID 23079035Allyl-1-benzotriazolyl carbonate

Product 1

HCID 18617738HCID 18617738, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a suspension of 5-(2-amino-ethyl)3-cyano-indole (reference example 2) (925 mg, 5 mmol) in CH2Cl2/THF (20 mL, 1/1) is added N,N-diisopropylethylamine (869 mL, 5 mmol) followed by allyl-1-benzotriazolyl carbonate (1.096 g, 5 mmol). The resulting mixture is stirred for 25 minutes then concentrated. The residue is purified by flash chromatography (eluting with 7% MeOH in CH2Cl2) to give 1.27 g of product as a white solid. 1H NMR (CDCl3) d 2.92 (t, J=7 Hz, 2H), 3.50 (q, J=7 Hz, 2H), 4.53 (d, J=5 Hz, 2H), 4.79 (bs, 1H), 5.18 (d, J=10 Hz, 1H), 5.26 (d, J=17 Hz, 1H), 5.87 (m, 1H), 7.10 (dd, J=8,1 Hz, 1H), 7.34 (d, J=8 Hz, 1H), 7.54 (s, 1H), 7.67 (d, J=1 Hz, 1H), 9.08 (bs, 1H). MS (EI) m/z 269 (M+).

Workup

  1. concentrationthen concentrated
  2. customThe residue is purified by flash chromatography (eluting with 7% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4dce7198faca4044986eb3188b20ff13
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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