Trimethylsilyl isocyanate → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxamide

HRID 1947841Notes

Reaction equation

HRID 1947841 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[CH3:8][C:9]1([CH3:22])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=2)[O:10]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:15][C:13]1([CH3:14])[C:9]([CH3:22])([CH3:8])[O:10][B:11]([C:16]2[CH2:17][CH2:18][N:19]([C:6]([NH2:5])=[O:7])[CH2:20][CH:21]=2)[O:12]1

Participants

6

Reactant 4

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 211054611,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 672569304-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyl isocyanate (0.2205 mL, 1.629 mmol) was added to a room temperature solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (200.0 mg, 0.8145 mmol) and DIPEA (0.5675 mL, 3.258 mmol) in DCM (10 mL). The mixture was stirred for 3 hours, after which, it was partioned between DCM and sat. NaHCO3. The organic layer was concentrated in vacuo to afford the title compound as a tan solid.

Workup

  1. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0a45d0858f62462fa8604be583709aa7
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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