Bromide ion → HCID 86727405, compound

HRID 519041Notes

Reaction equation

HRID 519041 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14](B4OC(C)(C)C(C)(C)O4)=[CH:13][C:12]=3[N:3]12.[Br-].[CH2:27]([CH:34]1[N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][CH:37]=[C:36](OS(C(F)(F)F)(=O)=O)[CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH2:27]([CH:34]1[N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][CH:37]=[C:36]([C:14]2[CH:15]=[CH:16][C:11]3[O:10][CH2:9][C:4]4=[N:5][NH:6][C:7](=[O:8])[CH:2]([CH3:1])[N:3]4[C:12]=3[CH:13]=2)[CH2:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 86727406HCID 86727406, compoundHCID 86727407HCID 86727407, compound

Product 1

HCID 86727405HCID 86727405, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one (prepared from the corresponding bromide (Preparation #1, Step D) following similar procedure as describe in Example #109, Step B, 0.103 g, 0.3 mmol), tert-butyl 6-benzyl-4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.253 g, 0.6 mmol), Pd(dppf)Cl2—CH2Cl2 complex (0.073 g, 0.09 mmol) and K2CO3 (0.124 g, 0.9 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was heated at 90° C. for 10 h. The reaction was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by PTLC (eluting with 50% EtOAc in petroleum ether) to give tert-butyl 6-benzyl-4-(1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.147 g, 99%). LC/MS (Table 1, Method 2) Rt=1.308 min; MS m/z: 489 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by PTLC (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c04b96b4e0024ec3ab3c81e7a4135def
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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