1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

HRID 1876850Notes

Reaction equation

HRID 1876850 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15]([CH:17]=[C:18]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)#[N:16].N12CCCN=C1CCCCC2>C(#N)C>[C:15]([CH2:17][C:18]1([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)#[N:16]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 457892161-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine

Product 1

HCID 67457197tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3.06 g, 0.0158 mol) in acetonitrile (50 mL) was added tert-butyl 3-(cyanomethylene)azetidine-1-carboxylate (3.06 g, 0.0158 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.36 mL, 0.0158 mol). The resulting mixture was stirred at room temperature overnight. After evaporating to dryness, the residue was purified on silica gel, eluting with 0-100% EtOAc in hexanes, to give the desired product (5.40 g, 88%). LCMS (M+H) 389.1.

Workup

  1. customAfter evaporating to dryness
  2. customthe residue was purified on silica gel
  3. washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-f872d9bac4454eac9f2afba9b3d23755
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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