Ammonium Hydroxide → (5-Sulfamoylpyridin-3-yl)boronic acid

HRID 1927964Notes

Reaction equation

HRID 1927964 reaction equation
Cl[N:2]1C(=O)CCC1=O.CN1CC[O:15][B:14]([C:18]2[CH:19]=[C:20]([S:24]([O-:26])=[O:25])[CH:21]=[N:22][CH:23]=2)[O:13]CC1.[Li+].[OH-].[NH4+]>C(Cl)Cl>[S:24]([C:20]1[CH:21]=[N:22][CH:23]=[C:18]([B:14]([OH:15])[OH:13])[CH:19]=1)(=[O:26])(=[O:25])[NH2:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 31398ChlorosuccinimideHCID 68697968Lithium 5-(6-methyl-[1,3,6,2]dioxazaborocan-2-yl)-pyridine-3-sulfinate

Product 1

HCID 57415702(5-Sulfamoylpyridin-3-yl)boronic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3) N-Chlorosuccinimide (0.937 g, 7.01 mmol) was added to a suspension of the above prepared lithium 5-(6-methyl-[1,3,6,2]dioxazaborocan-2-yl)-pyridine-3-sulfinate (2 g, 7.24 mmol) in CH2Cl2 (14 mL) and the mixture was stirred for 2 h at rt.A solution of 25% ammonium hydroxide (1.00 mL, 13.4 mmol) was added and the mixture was stirred again for 2 h at rt, then completely evaporated to give the title compound as an off-white solid (1.28 g, 88%) (according to Bioorg. Med. Chem. 2005, 13, 2305-2312). MS (ISP) 201.4 [(M−H)−].

Workup

  1. stirringthe mixture was stirred again for 2 h at rt
  2. customcompletely evaporated

Sources & evidence

ORD record
ord-2fc3926302b043389864c5ee28e5d62e
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…