Cesium carbonate → HCID 86728241, compound

HRID 1776831Notes

Reaction equation

HRID 1776831 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[F: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]([F:17])=[C:8]3[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 86728240HCID 86728240, compound

Product 1

HCID 86728241HCID 86728241, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 6-chloro-2-(3-fluoro-1H-indol-2-yl)pyridin-3-ol (120 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-chloro-12-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (60 mg, yield: 47.6%). 1H-NMR (CDCl3, 400 MHz) δ 7.63 (d, J=8.0 Hz, 2H), 7.06˜7.28 (m, 4H), 5.76 (s, 2H). MS (M+H)+: 275/277.

Workup

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

Sources & evidence

ORD record
ord-745c61766c634cdaa80af37ca8615b7e
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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