Potassium Carbonate → HCID 86727369, compound

HRID 519012Notes

Reaction equation

HRID 519012 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][C:32]1(C)[C:36](C)(C)OB(C(C)=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[C:32]([CH3:36])=[CH2:31])[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 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 86727364HCID 86727364, compound

Product 1

HCID 86727369HCID 86727369, compoundYield 76.4%

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 (Example #75, Step A, 0.05 g, 0.104 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.035 g, 0.209 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloride dichloromethane complex (0.017 g, 0.021 mmol) and K2CO3 (0.029 g, 0.209 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 and the filtrate was concentrated in vacuo. The residue was purified by preparative-TLC (eluting with 50% EtOAc in petroleum ether) to give 4-(7-isopropenyl-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 (0.035 g, 76%) as a pale-white solid. LC/MS (Table 1, Method 5) Rt=3.653 min.; MS m/z: 441 [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-bb0f0a3861d54f2e8cb6b20a97cd3838
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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