1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → 2-(3-Sulfamoyl-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester

HRID 1438103Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[C:19]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([S:23](=[O:25])(=[O:24])[NH2:26])[CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 92 °C

Procedure

A mixture of 3A, 3-bromobenzene sulfonamide (0.1 g, 0.4 mmol) in DME (6 mL) and 2.0 M Na2CO3 (0.8 mL) was degassed by bubbling argon for 5 min. To this solution, Pd(PPh3)4 (28 mg, 0.025 mmol) was added. The mixture was heated at 92° C. for 3 h. After cooling to rt, it was extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (hexanes/EtOAc=3/1) to give 3B (293 mg, 90% yield) as a semi-solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9H) 4.88 (s, 2H) 6.23 (m, 1H) 7.36 (m, 1H) 7.47 (t, J=7.69 Hz, 1H) 7.55 (m, 1H) 7.83 (d, J=8.35 Hz, 1H) 7.90 (s, 1H).

Workup

customwas degassed
customby bubbling argon for 5 min
temperatureAfter cooling to rt
extractionit was extracted with EtOAc
dry with materialdried over Na2SO4
customThe crude product was purified by silica gel chromatography (hexanes/EtOAc=3/1)

Sources & evidence

ORD record: ord-f941b7d60f25474da30523f0da157186
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622585B2

Reaction notes

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