HCID 89739148, compound → HCID 89739131, compound

HRID 2206575Notes

Reaction equation

HRID 2206575 reaction equation
Br[C:2]1[C:9]2[S:8][CH:7]=[N:6][C:5]=2[N:4]([CH:10]([CH3:14])[CH2:11][O:12][CH3:13])[C:3]=1[CH3:15].[C:16]([Cu])#[N:17]>CN(C)C=O>[CH3:13][O:12][CH2:11][CH:10]([N:4]1[C:5]2[N:6]=[CH:7][S:8][C:9]=2[C:2]([C:16]#[N:17])=[C:3]1[CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 89739148HCID 89739148, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 89739131HCID 89739131, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-bromo-4-(1-methoxypropan-2-yl)-5-methyl-4H-pyrrolo[2,3-d]thiazole (2.0 g, 6.92 mmol) in anhydrous N,N-dimethylformamide (15 mL) was added cyano copper (1.24 g, 13.84 mmol). The resulting reaction mixture was heated to 150° C. and allowed to stir for 2 hours at 150° C. The reaction mixture was washed with water and brine, and extracted with acetic ester (30 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 30:1-20:1-10:1) to give the title compound (1.0 g, 62%) as yellow oil. LCMS (M+H+) m/z: calc'd. 235.08. found 236.0.

Workup

  1. customThe resulting reaction mixture
  2. washThe reaction mixture was washed with water and brine
  3. extractionextracted with acetic ester (30 mL×3)
  4. dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatograph on silica gel
  8. washeluted with (petrol ether/acetic ester 30:1-20:1-10:1)

Sources & evidence

ORD record
ord-aaf46fe8e411430e93f4a7c693f6611d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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