Potassium Carbonate → HCID 86727609, compound

HRID 519193Notes

Reaction equation

HRID 519193 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2Br)[O:25][CH2:24][C:23]2[N:18]3[CH:19]([CH3:39])[C:20](=[O:38])[N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:22]=2)[CH2:10][C@@H:9]1[CH3:40])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[F:41])[O:25][CH2:24][C:23]2[N:18]3[CH:19]([CH3:39])[C:20](=[O:38])[N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:22]=2)[CH2:10][C@@H:9]1[CH3:40])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 86727610HCID 86727610, compound

Product 1

HCID 86727609HCID 86727609, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2S,5R)-4-[7-bromo-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.4 g, 0.626 mmol), 2-fluorophenylboronic acid (0.105 g, 0.752 mmol), K2CO3 (0.173 g, 1.253 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.101 g, 0.125 mmol) in dioxane (8 mL) and water (2 mL) was stirred at 90° C. for 2.5 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-20% EtOAc in petroleum ether) to give (2S,5R)-4-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.250 g, 61%) as a solid. LC/MS (Table 1, Method 25) Rt=1.143 min.; MS m/z: 654 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 0-20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-4b964e74a4f84af4a6ff76f7028b28be
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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