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Diisopropylethylamine → 2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide

HRID 881732
Notes
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Reaction equation

HRID 881732 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.[CH3:17][C:18]1[O:19][C:20]([C:26]([F:29])([F:28])[F:27])=[C:21]([C:23](O)=[O:24])[N:22]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Cl-].[Na+].O.O>[CH3:17][C:18]1[O:19][C:20]([C:26]([F:29])([F:27])[F:28])=[C:21]([C:23]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:24])[N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 27756512-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86700837
2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide
Yield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (420 mg, 1.917 mmol) in anhydrous DMF (9.6 mL) was added 2-methyl-5-(trifluoromethyl)oxazole-4-carboxylic acid (449 mg, 2.300 mmol) followed by DIPEA (1.0 mL, 5.75 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (875 mg, 2.300 mmol) was added and the mixture stirred at room temperature for 16 hours. The mixture was taken up in 1:1 mixture of brine and water and extracted with EtOAc. The organic portion was dried over sodium sulfate, filtered and concentrated to afford a brown oil, which was purified by flash column chromatography to afford the title compound as pale yellow solid after drying (360 mg, 47% yield). LC/MS, ESI-MS(+): 397.1, RT: 1.49 (Condition E).

Workup

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a brown oil, which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-acddda486ab8432eba5665004956429a
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993619B2

Reaction notes

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