Sodium Carbonate → 4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1404233Notes

Reaction equation

HRID 1404233 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH:9]1B1OC(C)(C)C(C)(C)O1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:34][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=3)=[N:32][CH:31]=2)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[O:34][C:33]([NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=4)=[N:32][CH:31]=3)=[CH:28][CH:29]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66615833[5-(4-Bromo-phenyl)-oxazol-2-yl]-(3-chloro-phenyl)-amineHCID 68807496811439-53-9

Product 1

HCID 666158304-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Preparation of -(4,4,5, 5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester has been described [Tet. Lett. 41(19), 3705-3708, 2000]. The boronate ester (1.1 g, 3.6 mmol, 1.5 equiv) and [5-(4-bromo-phenyl)-oxazol-2-yl]-(3-chloro-phenyl)-amine (0.84 g, 2.4 mmol, 1.0 equiv) were dissolved in 12 mL DME and then charged with 3 mL of a 2M Na2CO3 solution. Pd(Ph3)4 on polystyrene resin (0.72 g, 0.072 mmol) was added, and the suspension was sparged with nitrogen for 10 min, then heated to 100° C. overnight. The reaction was then filtered to remove catalyst, and following solvent removal the product was triturated with hexanes and ether to afford the title compound: (M+H)+ 452.1.

Workup

  1. customthe suspension was sparged with nitrogen for 10 min
  2. filtrationThe reaction was then filtered
  3. customto remove catalyst
  4. customsolvent removal the product
  5. customwas triturated with hexanes and ether

Sources & evidence

ORD record
ord-f7c15e5f4911408b844c72a28a55cba7
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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