Triethylamine → HCID 118200992, compound

HRID 1048695Notes

Reaction equation

HRID 1048695 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29]>ClCCl>[C:28](=[O:29])([O:19][CH2:18][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[C:9]=1[C:8]#[C:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[O:30][CH2:31][CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 90031842HCID 90031842, compound

Product 1

HCID 118200992HCID 118200992, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.1 g (0.403 mmol) of (3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl) methanol were solubilised in 3 ml of dichloromethane with magnetic stirring. 0.084 ml (0.604 mmol) of triethylamine and 0.059 ml (0.443 mmol) of isobutyl chloroformate were added. The mixture was stirred at r.t. for 15 min before being concentrated in vacuo. The residue was taken up in 10 ml of diisopropyl ether and a solid was isolated by filtration. The solid was purified by preparative HPLC and 0.084 g (yield=59%) of isobutyl ((3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methyl) carbonate were obtained as a pale yellow solid. LC-MS: m/z=349 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.70 (d, J=6.8 Hz, 1H), 7.79-7.65 (m, 3H), 7.60-7.45 (m, 4H), 7.23 (td, J=6.8, 1.1 Hz, 1H), 5.42 (s, 2H), 3.91 (d, J=6.6 Hz, 2H), 1.95-1.80 (m, 1H), 0.86 (d, J=6.7 Hz, 6H).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customa solid was isolated by filtration
  3. customThe solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-2cc67df7253c428d97b9583f5b45a6b5
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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