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1,2-Dimethoxyethane → Ethyl 2-(2-((tert-butoxycarbonyl)(cyclopropylmethyl)amino)pyridin-4-yl)oxazole-4-carboxylate

HRID 632814
Notes
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Reaction equation

HRID 632814 reaction equation
[CH:1]1([CH2:4][N:5]([C:13]2[CH:18]=[C:17](B3OC(C)(C)C(C)(C)O3)[CH:16]=[CH:15][N:14]=2)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:3][CH2:2]1.Br[C:29]1[O:30][CH:31]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:33]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>O>[C:8]([O:7][C:6]([N:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[C:13]1[CH:18]=[C:17]([C:29]2[O:30][CH:31]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:33]=2)[CH:16]=[CH:15][N:14]=1)=[O:12])([CH3:9])([CH3:10])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 26370035Ethyl 2-bromo-1,3-oxazole-4-carboxylateHCID 131735466Tert-butyl (cyclopropylmethyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate

Product 1

HCID 118060817Ethyl 2-(2-((tert-butoxycarbonyl)(cyclopropylmethyl)amino)pyridin-4-yl)oxazole-4-carboxylate
Yield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl (cyclopropylmethyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate (48.3 g), ethyl 2-bromo-1,3-oxazole-4-carboxylate (25.8 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane complex (4.79 g), potassium carbonate (32.4 g) and DME (489 mL)/water (98 mL) was stirred at 80° C. for 4 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (33.3 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2811331ff5644e378f6095945fc4d42e
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321757B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes