Cesium carbonate → HCID 71295679, compound

HRID 1776883Notes

Reaction equation

HRID 1776883 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]3[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=3[N:10]=2)[C:5]([OH:8])=[N:6][CH:7]=1.[C:18](=O)([O-])[O-].[Cs+].[Cs+].ClCI>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[O:8][CH2:18][N:13]3[C:12]4[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=4[N:10]=[C:9]3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 178517591HCID 178517591, compound

Product 1

HCID 71295679HCID 71295679, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)pyridin-2-ol (0.3 g, 1.02 mmol) and Cesium carbonate (0.663 g, 2.04 mmol) in DMF (10 mL), was heated to 100° C. Then chloroiodomethane (215 mg, 1.22 mmol) was added by dropwise, the react mixture was stirred at 100° C. for 30 minutes. The solvent was removed off and the resulting residue was purified using flash column (petroleum ether:EtOAc 3:1) to provide 2-bromo-8,9,10,11-tetrahydro-6H-benzo[4,5]imidazo[1,2-c]pyrido[3,2-e][1,3]oxazine (50 mg, yield 16%) as a solid. 1HNMR (400 MHz, CDCl3): δ=8.30 (d, J=2.4 Hz, 1H), 8.20 (d, J=2.4 Hz, 1H), 5.87 (s, 2H), 2.66˜2.68 (m, 2H), 2.58˜2.61 (m, 2H), 1.87˜1.88 (m, 4H). MS (M+H)+: 306/308.

Workup

  1. customThe solvent was removed off
  2. customthe resulting residue was purified

Sources & evidence

ORD record
ord-9c9064d302844b08bf2457d6e9eebb51
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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