Cesium carbonate → HCID 86728231, compound

HRID 1776812Notes

Reaction equation

HRID 1776812 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:10](=[N:11][C:12]([O:17][CH3:18])=[CH:13][CH:14]=3)[CH:9]=2)[C:5]([OH:19])=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[Cs+].[Cs+].ClCI>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:20][N:16]3[C:15]4[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[N:11][C:10]=4[CH:9]=[C:8]3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 136341364HCID 136341364, compound

Product 1

HCID 86728231HCID 86728231, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 6-chloro-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-3-ol (200 mg, 0.727 mmol) and Cs2CO3 (472 mg, 1.45 mmol) in DMF (15 mL) was added chloroiodomethane (192 mg, 1.09 mmol) in DMF (2 mL) dropwise at 100° C. under N2. The mixture was stirred at 100° C. for 1 hour. The mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine and dried over Na2SO4. After concentrated, the resulting residue was purified using Pre-TLC to provide 2-chloro-10-methoxy-6H-pyrido[2,3-e]pyrido[2′,3′:4,5]pyrrolo[1,2-c][1,3]oxazine (110 mg, yield: 52%). 1H-NMR (CDCl3, 400 MHz) 7.44 (d, J=8.8 Hz, 1H), 7.26 (d, J=8.8 Hz, 1H), 7.16 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 5.81 (s, 2H), 3.95 (s, 3H). MS (M+H)+: 288/290.

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-329153b9bf9c4e0a99e71d11189bff6c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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