2-Methylquinoline → (E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

HRID 1772592Notes

Reaction equation

HRID 1772592 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([CH:11]=O)[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1.[CH3:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.Br[Si](C)(C)C>CN(C=O)C>[Br:1][C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:19]/[C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 70602-MethylquinolineHCID 76113BromotrimethylsilaneHCID 1177281135-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehyde

Product 1

HCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 2a (800 mg, 2.58 mmol) in DMF (10 mL) was added 2-methylquinoline (600 mg, 4.20 mmol) and bromotrimethylsilane (960 mg, 8.89 mmol). The reaction mixture was stirred in a 20 mL sealed tube at 90° C. for 4 h. After cooling to rt, the reaction was quenched with MeOH (20 mL). The solids were collected by filtration and washed with Et2O to obtain compound 2b as a red solid (1.05 g, 85% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H18BrN5O: 436.1 (M+H). found: 436.1.

Workup

  1. customsealed tube at 90° C. for 4 h
  2. customthe reaction was quenched with MeOH (20 mL)
  3. filtrationThe solids were collected by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-d0ae6533bf0f44439cb6e447ce92593d
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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