HCID 67172151, compound → HCID 67174787, compound

HRID 1256058Notes

Reaction equation

HRID 1256058 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=3)(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1>[Pd].CCO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)(=[O:13])=[O:14])=[CH:16][C:17]=1[C:24]([F:25])([F:27])[F:26]

Participants

4

Reactant 1

HCID 67172151HCID 67172151, compound

Product 1

HCID 67174787HCID 67174787, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-nitro-3-trifluoromethyl-benzenesulfonamide (212 mg, 0.53 mmol), 10% Pd/C (50 mg), and abs. EtOH (100 mL) was shaken in a Parr apparatus at rt under an atmosphere of H2 (50 psi) for 2 h. The mixture was filtered through Celite (washing with EtOH) and then a 0.2 μM filter. The filtrate was concentrated in vacuo at 40° C. and the residue was recrystallized (MeCN/H2O) to give the title compound as a white solid; yield 122 mg (62%). mp 178-179° C.; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.98 (s, 1H), 9.22 (s, 1H), 7.65-7.64 (m, 1H), 7.54-7.51 (m, 1H), 7.48-7.47 (m, 1H), 7.28-7.26 (m, 1H), 7.16-7.14 (m, 1H), 6.82-6.79 (m, 1H), 6.49 (s, 2H), 4.88 (s, 2H); 19F NMR (376 MHz, DMSO-d6) δ (ppm): −63.0 (s); MS (ESI) m/z=371 (M−1, negative); HPLC purity: 98.02% (MaxPlot 200-400 nm), 98.34% (220 nm).

Workup

  1. filtrationThe mixture was filtered through Celite (washing with EtOH)
  2. filtrationa 0.2 μM filter
  3. concentrationThe filtrate was concentrated in vacuo at 40° C.
  4. customthe residue was recrystallized (MeCN/H2O)

Sources & evidence

ORD record
ord-35b457545aa64c4980d689099c428ced
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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