Methyl vinyl sulfone → HCID 66760162, compound

HRID 389456Notes

Reaction equation

HRID 389456 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)[O:3]1.[CH3:21][S:22]([CH:25]=[CH2:26])(=[O:24])=[O:23].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:21][S:22]([CH2:25][CH2:26][N:17]1[CH2:18][CH2:19][CH:14]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:20])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:15][CH2:16]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 81531DiisopropylethylamineHCID 57812229HCID 57812229, compound

Product 1

HCID 66760162HCID 66760162, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine (500 mg, 1.80 mmol), (methylsulfonyl)ethene (212 mg, 1.99 mmol), and DIPEA (500 mL, 2.87 mmol) in DMF (6 mL) was stirred at 25° C. for 30 min. The reaction mixture was then concentrated in vacuo to a solid and then purified by flash chromatography (0 to 5% MeOH:EtOAc) to yield 74.5 mg (11%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.98 (s, 1H), 7.59 (s, 1H), 4.17 (tt, J=10.36, 5.05 Hz, 1H), 3.30 (s, 2H), 3.05 (s, 3H), 2.98 (d, J=11.62 Hz, 2H), 2.74 (t, J=6.57 Hz, 2H), 2.13 (td, J=11.37, 3.28 Hz, 2H), 1.88-2.00 (m, 4H), 1.25 (s, 12H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo to a solid
  2. custompurified by flash chromatography (0 to 5% MeOH:EtOAc)

Sources & evidence

ORD record
ord-cfbf9ba31f15432d9339c829f8e7113e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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