Cesium carbonate → HCID 67077862, compound

HRID 1959553Notes

Reaction equation

HRID 1959553 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([Cl:16])[C:13]=1[CH:14]=[O:15].[S:17]1[CH:21]=[CH:20][N:19]=[C:18]1[SH:22]>C1COCC1>[Cl:16][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([S:22][C:18]2[S:17][CH:21]=[CH:20][N:19]=2)[C:13]=1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 178527881HCID 178527881, compound

Product 1

HCID 67077862HCID 67077862, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cs2CO3 (0.22 g, 0.68 mmol) was added to a solution of 3,5-dichloro-pyridine-4-carbaldehyde (0.10 g, 0.57 mmol) and thiazole-2-thiol (0.10 g, 0.85 mmol) in THF (10 mL). After stirring at room temperature overnight, the solvent was removed in vacuo and saturated aqueous NaCl solution (20 mL) and EA (40 mL) were added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo and the residue was used in the following step without further purification. The aldehyde group in 3-chloro-5-(thiazol-2-ylsulfanyl)-pyridine-4-carbaldehyde was reduced as described for the synthesis of (3,5-dichloro-pyridin-4-yl)-methanol to give [3-chloro-5-(thiazol-2-ylsulfanyl)-pyridin-4-yl]-methanol which was used in the following step without further purification. Conversion of [3-chloro-5-(thiazol-2-ylsulfanyl)-pyridin-4-yl]-methanol into 3-chloro-4-chloromethyl-5-(thiazol-2-ylsulfanyl)-pyridine according to the synthesis of 3,5-dichloro-4-chloromethyl-pyridine and subsequent reaction with 2-methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol according to the synthesis of 8-(3,5-dichloro-pyridin-4-ylmethoxy)-4-imidazol-1-yl-2-methylquinoline yielded the title compound as the TFA salt. MS (m/z): 480.2 [M+H+].

Workup

  1. customthe solvent was removed in vacuo and saturated aqueous NaCl solution (20 mL) and EA (40 mL)
  2. additionwere added to the reaction mixture
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue was used in the following step without further purification
  7. customas described for the synthesis of (3,5-dichloro-pyridin-4-yl)-methanol

Sources & evidence

ORD record
ord-d776613f44c0440c938e714c8325ef96
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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