Diisopropylethylamine → 2-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one

HRID 872176Notes

Reaction equation

HRID 872176 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:28]([OH:30])=O)=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([B:18]3[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]3)[C:13]=2[CH3:27])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([C:5]1[S:6][C:7]2[C:28](=[O:30])[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([B:18]4[O:19][C:20]([CH3:26])([CH3:25])[C:21]([CH3:23])([CH3:24])[O:22]4)[C:13]=3[CH3:27])[CH2:10][C:8]=2[N:9]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 666345362-tert-Butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylic acid

Product 1

HCID 666348992-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-tert-butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylic acid 109e (430.37 mg, 0.0010000 mol) in methylene chloride (10 mL) was added N,N-diisopropylethylamine (870.91 uL, 5.0 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uranium hexafluorophosphate (1.1407 g, 0.0030000 mol). The mixture was stirred at room temperature overnight. The reaction mixture was extracted with water. The organic layer was separated, and dried with anhydrous magnesium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified on silica eluted with a gradient of 0 to 20% Ethyl acetate in Heptane to afford 2-tert-butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one 109f (163 mg, 40%).

Workup

  1. extractionThe reaction mixture was extracted with water
  2. customThe organic layer was separated
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified on silica
  7. washeluted with a gradient of 0 to 20% Ethyl acetate in Heptane

Sources & evidence

ORD record
ord-0b74613d208f4db78c95c7b5a2eab5eb
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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