6-Bromo-4-chloroquinoline → HCID 118324082, compound

HRID 1778307Notes

Reaction equation

HRID 1778307 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:12].[Li]CCCC.CON(C)[C:21]([C:23]1[N:24]=[CH:25][S:26][CH:27]=1)=[O:22]>C1COCC1>[Cl:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:21]([C:23]3[N:24]=[CH:25][S:26][CH:27]=3)=[O:22])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 51395376-Bromo-4-chloroquinolineHCID 16203794N-methoxy-N-methylthiazole-4-carboxamideHCID 178418339Butyllithium

Product 1

HCID 118324082HCID 118324082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-bromo-4-chloroquinoline (0.459 g, 1.89 mmol) in THF (8 mL) was added n-BuLi (1.12 mL, 1.80 mmol, 1.6M in hexane) at −78° C. under argon and the resulting mixture was stirred for 2 hr. A solution of N-methoxy-N-methylthiazole-4-carboxamide (0.39 g, 2.27 mmol) in THF (2 mL) was added and the resulting mixture was allowed to warm to room temperature and stirred at room temperature for 2 hr. The reaction mixture was quenched with ice and saturated NH4Cl. The aqueous layer was extracted with CH2Cl2. The combined organics were concentrated and purified by column chromatography (40-50% EtOAc/hexanes) to yield (4-chloroquinolin-6-yl)(thiazol-4-yl)methanone. (ES, m/z) [M+H]+ 275, 277.

Workup

  1. stirringstirred at room temperature for 2 hr
  2. customThe reaction mixture was quenched with ice and saturated NH4Cl
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. concentrationThe combined organics were concentrated
  5. custompurified by column chromatography (40-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-35a7db15be464ba59765204941100c3e
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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