Potassium Carbonate → HCID 86728227, compound

HRID 1776797Notes

Reaction equation

HRID 1776797 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:17])=[CH:4][CH:3]=1.[C:18]([O-])([O-])=O.[K+].[K+].ClCI>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][CH2:18][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH:16]=[C:8]3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11644ChloroiodomethaneHCID 86728225HCID 86728225, compound

Product 1

HCID 86728227HCID 86728227, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (480 mg, 2.0 mmol) and K2CO3 (1.38 g, 10.0 mmol) in DMF (50 mL) stirring at 100° C., chloroiodomethane (386 mg, 2.2 mmol) in DMF (10 mL) was added dropwise. After addition, the mixture was allowed to stir for another 0.5 hours. The mixture was then diluted with water (100 mL) and extracted with EtOAc (100 mL*3). The organic layer was washed with brine (100 mL*3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=3:1) to provide the product 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (260 mg, yield: 50.7%). 1H-NMR (CDCl3, 400 MHz) δ 7.63 (d, J=8.0 Hz, 1H), 7.22˜7.27 (m, 3H), 7.19 (d, J=2.4 Hz, 1H), 7.08˜7.12 (m, 2H), 5.86 (s, 2H). MS (M+H)+: 257/259.

Workup

  1. additionAfter addition
  2. extractionextracted with EtOAc (100 mL*3)
  3. washThe organic layer was washed with brine (100 mL*3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-f243f7ff0d46462891570ff43655fb7c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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