Cesium carbonate → HCID 86728239, compound

HRID 1776828Notes

Reaction equation

HRID 1776828 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[Cl:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:18])=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[Cs+].[Cs+].ClCI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]([Cl:17])=[C:8]3[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 86728238HCID 86728238, compound

Product 1

HCID 86728239HCID 86728239, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 6-chloro-2-(3-chloro-1H-indol-2-yl)pyridin-3-ol (128 mg, 0.46 mmol) and Cs2CO3 (452 mg, 1.39 mmol) in DMF (6 mL) was stirred at 100° C. (internal temperature), then chloroiodomethane (173 mg, 0.92 mmol) in DMF (1 mL) was added dropwise. After the reaction was completed according to TLC, the mixture was filtered and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=4:1) to provide 2,12-dichloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (100 mg, yield: 75.2%). 1H-NMR (CDCl3, 400 MHz) δ 7.65 (d, J=8.0 Hz, 1H), 7.11˜7.31 (m, 5H), 5.82 (s, 2H). MS (M+H)+: 291/293.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified

Sources & evidence

ORD record
ord-2260497e36b849fbbf911c93da37435f
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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