Dimethylformamide → HCID 67958128, compound

HRID 527632Notes

Reaction equation

HRID 527632 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][C:10]2[C:9]([OH:12])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][O:3]1.CN(C=O)C.Cl[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1>>[CH3:1][C:2]1([CH3:13])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=2)[CH2:4][O:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 783082-Chloro-5-nitropyridineHCID 67958030HCID 67958030, compound2×

Product 1

HCID 67958128HCID 67958128, compoundYield 83.2%

Conditions

Temperature
80 °C

Procedure

To a solution of 3,3-dimethylisochroman-5-ol (Intermediate 170, 65 mg, 0.36 mmol) in dry DMF (3 ml) potassium carbonate (207 mg, 1.5 mmol) and then 2-chloro-5-nitropyridine (50.8 mg, 0.32 mmol) were added and the reaction mixture was stirred for 2 hours at 80° C. After cooling the reaction mixture was quenched with water (2 ml), diluted with brine (10 ml) and extracted with ethyl acetate (2×20 ml). The organic layer was dried over sodium sulfate, filtered and evaporated affording the title compound (80 mg) as an orange solid that was used in the next step as crude without further purification.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas quenched with water (2 ml)
  3. additiondiluted with brine (10 ml)
  4. extractionextracted with ethyl acetate (2×20 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c1360244efdf408c9e181f5746852b96
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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