Potassium Carbonate → HCID 86727468, compound

HRID 519096Notes

Reaction equation

HRID 519096 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2Br)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][C:25]3[O:24][CH2:23][C:22]4=[N:21][NH:20][C:19](=[O:29])[CH:18]([CH3:30])[N:17]4[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86727364HCID 86727364, compound

Product 1

HCID 86727468HCID 86727468, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.02 g, 0.042 mmol), phenylboronic acid (0.01 g, 0.083 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloride dichloromethane complex (0.007 g, 0.008 mmol) and K2CO3 (0.012 g, 0.083 mmol) in dioxane (1 mL) and water (0.2 mL) was heated to reflux for 8 h. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether) to give tert-butyl-4-(1-methyl-2-oxo-8-phenyl-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.02 g, 100%) as a pale-white solid. LC/MS (Table 1, Method 3) Rt=1.596 min.; MS m/z: 477 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a2e05d868bcc4c3a9ebdd15b283e8135
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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