Potassium Carbonate → HCID 86727363, compound

HRID 519006Notes

Reaction equation

HRID 519006 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(OC(N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][CH:27]=2)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 86727364HCID 86727364, compound

Product 1

HCID 86727363HCID 86727363, compoundYield 87.4%

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 (Preparation #1, Step D, 1.70 g, 5.74 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.55 g, 11.48 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloride dichloromethane complex (0.494 g, 0.675 mmol) and K2CO3 (1.58 g, 11.48 mmol) in dioxane (10 mL) and water (2 mL) was heated to reflux for 6 h. The reaction mixture was cooled to ambient temperature and filtered through a pad of Celite®. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 40% EtOAc in petroleum ether) to give 4-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (2.0 g, 87%) as a pale white solid. LC/MS (Table 1, Method 3) Rt=1.398 min.; MS m/z: 399 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-1d22f7329c304e6ca76b6c35eb9aff18
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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