Potassium Carbonate → HCID 86727367, compound

HRID 519010Notes

Reaction equation

HRID 519010 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].[CH3:31]B1OB(C)OB(C)O1.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[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[CH3:31])[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]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 86727364HCID 86727364, compound

Product 1

HCID 86727367HCID 86727367, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A degassed 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 (0.08 g, 0.167 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.042 g, 0.334 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloride dichloromethane complex (0.027 g, 0.033 mmol) and K2CO3 (0.046 g, 0.334 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 4-(4,7-dimethyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.03 g, 43%) as a pale white solid. LC/MS (Table 1, Method 3) Rt=1.415 min.; MS m/z: 415 [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-de492d28a733486e8b1615a6fe17e682
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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