Water → HCID 75409785, compound

HRID 2366282Notes

Reaction equation

HRID 2366282 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][C:11]2[C:12]([Cl:18])=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1.[Cu][C:20]#[N:21].O>CN1C(=O)CCC1>[Cl:8][C:4]1[C:3]([C:9]2[S:10][C:11]3[C:12]([Cl:18])=[N:13][CH:14]=[CH:15][C:16]=3[N:17]=2)=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:20]#[N:21]

Participants

5

Reactant 3

HCID 962WaterHCID 86669015HCID 86669015, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 75409785HCID 75409785, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 2-(2-bromo-6-chlorophenyl)-4-chlorothiazolo[5,4-c]pyridine (1.48 g, 4.11 mmol) and copper(I) cyanide (0.45 g, 5.0 mmol) in NMP (20 mL) was heated at 150° C. for 20 minutes. After cooling to room temperature, the mixture was poured into water (250 mL) and the insoluble material was collected by filtration. The solid was then suspended in EtOAc (300 mL) and, after vigorous stirring, was collected by filtration. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 25-33% diethyl ether in pentane followed by 0-10% MeOH in DCM to afford the title compound as a pale yellow solid (0.364 g, 29% yield). LCMS (Method E): RT=3.59 min, m/z: 306 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe insoluble material was collected by filtration
  3. filtrationafter vigorous stirring, was collected by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resultant residue was purified by column chromatography on silica gel eluting with 25-33% diethyl ether in pentane

Sources & evidence

ORD record
ord-7762ceae2ca84a48bb69454c8172c653
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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