Ethyl isocyanate → HCID 58020008, compound

HRID 1632085Notes

Reaction equation

HRID 1632085 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][NH2:16])=[N:13][CH:14]=2)[O:3]1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH2:18]([NH:20][C:21]([NH:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:17])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:14][N:13]=1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 516892Sodium BicarbonateHCID 547754641-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methanamine

Product 1

HCID 58020008HCID 58020008, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 50 mL round bottom flask was added C-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methylamine (I-161, 1 g, crude), pyridine (10 mL), and ethyl isocyanate (0.5 mL, 6.5 mmol). The reaction was stirred at room temperature for 30 minutes and then NaHCO3 (sat) was added. The product was extracted with 3×10 mL EtOAc and the combined organics were dried over Na2SO4, and concentrated. The residue was purified by flash column chromatography eluting with 50% acetone/dichloromethane—100% MeOH to afford 289 mg of I-162 as a brown oil in 22% yield.

Workup

  1. extractionThe product was extracted with 3×10 mL EtOAc
  2. dry with materialthe combined organics were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography
  5. washeluting with 50% acetone/dichloromethane—100% MeOH
  6. customto afford 289 mg of I-162 as a brown oil in 22% yield

Sources & evidence

ORD record
ord-a77f7683aec64264bb5f44444ea4c4b1
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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