Pyridine → HCID 22027852, compound

HRID 1047073Notes

Reaction equation

HRID 1047073 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.N1C=CC=CC=1.Cl[C:24]([O:26][CH3:27])=[O:25]>ClCCCl.CCOC(C)=O>[CH3:27][O:26][C:24](=[O:25])[NH:13][C:12]1[CH:14]=[CH:15][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 22027852HCID 22027852, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (150 mg, 0.685 mmol) and pyridine (0.277 mL, 3.43 mmol) in 1,2-dichloroethane (3.5 mL) was added methyl chloroformate (0.058 mL, 0.754 mmol) at 0° C. and stirred at 60° C. for 6 hours. The mixture was diluted with AcOEt, washed with 1N HCl, brine, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated to afford the desired product (198 mg, quant) as a pale yellow oil. 1HNMR (CDCl3) 400 MHz δ: 7.75 (d, J=8.6 Hz, 2H), 7.39 (d, J=8.6 Hz, 2H), 6.64 (br s, 1H), 3.78 (s, 3H), 1.34 (s, 12H).

Workup

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltrated through Celite pad
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-137ceec08fec473fb4a0d5f189683d79
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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