Methanol → HCID 67173761, compound

HRID 1256073Notes

Reaction equation

HRID 1256073 reaction equation
[OH:1][B:2]1[C:6](=[CH:7][C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[CH3:23])(=[O:13])=[O:12])=[CH2:9])[CH2:5][CH2:4][O:3]1.[CH3:24]O>[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:8]2[CH:9]=[CH:24][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)(=[O:13])=[O:12])=[C:15]([CH3:23])[CH:16]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86655203HCID 86655203, compound

Product 1

HCID 67173761HCID 67173761, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of N-[1-(2-hydroxy-[1,2]oxaborolan-3-ylidenemethyl)-vinyl]-2-methyl-4-nitro-benzenesulfonamide (300 mg, 0.86 mmol) and Pd/C (300 mg, 10% wet) in MeOH (20.0 mL) was placed under a hydrogen atmosphere at 50 psi at rt for 1 h. The solid catalyst was filtered off through a pad of Celite. The filtrate was then concentrated in vacuo and the residue was suspended in hot water. The solid product was filtered and dried to affording 40 mg (15%) of the title compound as a white solid. mp. 174-175° C.; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.90 (br. s., 1H), 9.15 (s, 1H), 7.51 (d, J=8.2 Hz, 1H), 7.40 (d, J=1.6 Hz, 1H), 7.21-7.16 (m, 1H), 7.14-7.09 (m, 1H), 6.34-6.28 (m, 2H), 5.81 (s, 2H), 4.83 (s, 2H), 2.38 (s, 3H); (ESI) m/z=317 (M−1, negative); HPLC purity: 96.23% (MaxPlot 200-400 nm), 97.5% (220 nm).

Workup

  1. filtrationThe solid catalyst was filtered off through a pad of Celite
  2. concentrationThe filtrate was then concentrated in vacuo
  3. filtrationThe solid product was filtered
  4. customdried

Sources & evidence

ORD record
ord-67562521eab04235b3333ed458cd38eb
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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