Dichloromethane → HCID 66966750, compound

HRID 1366239Notes

Reaction equation

HRID 1366239 reaction equation
[CH3:1][Si:2]([CH3:6])([CH3:5])[C:3]#[CH:4].N12CCN(CC1)CC2.Br[C:16]1[S:20][C:19]([C:21]2[N:22]=[C:23]3[N:27]([C:28]=2[NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:26]=[CH:25][S:24]3)=[CH:18][CH:17]=1.C(Cl)Cl>C(#N)C>[C:30]([NH:29][C:28]1[N:27]2[C:23]([S:24][CH:25]=[CH:26]2)=[N:22][C:21]=1[C:19]1[S:20][C:16]([C:4]#[C:3][Si:2]([CH3:6])([CH3:5])[CH3:1])=[CH:17][CH:18]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9237DabcoHCID 66111TrimethylsilylacetyleneHCID 66966772HCID 66966772, compound

Product 1

HCID 66966750HCID 66966750, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.1 g (3.5 mmol) tetrakis(triphenyl)phosphine-palladium(0), 17.2 g (175.4 mmol) trimethyl-silylacetylene and 7.9 g (70.2 mmol) 1,4-diazabicyclo[2.2.2]octane were consecutively added to a suspension of 12.5 g (35.1 mmol) 6-(5-bromothiophene-2-yl)-N-tert-butylimidazo[2,1-b]thiazole-5-amine in acetonitrile (150 ml). The reaction solution was heated for 72 h under reflux and subsequently concentrated in a vacuum. 3.0 g (7.9 mmol, 23%) N-tert-butyl-6-(5-((trimethylsilyl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine ([MH+] 374.1) was obtained by CC (DCM/AE 95:5).

Workup

  1. temperatureThe reaction solution was heated for 72 h
  2. temperatureunder reflux
  3. concentrationsubsequently concentrated in a vacuum

Sources & evidence

ORD record
ord-4aa45c09b2d9414ca3fbf7bd25f5dfe4
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

Loading…