Triisopropyl borate → HCID 66672775, compound

HRID 423563Notes

Reaction equation

HRID 423563 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][CH2:18][O:19][CH3:20])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C>C1COCC1>[CH3:20][O:19][CH2:18][CH2:17][NH:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([B:25]([OH:26])[OH:24])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 4378537HCID 4378537, compoundHCID 178418339Butyllithium

Product 1

HCID 66672775HCID 66672775, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5M in hexanes, 8.36 mL, 20.89 mmol) was added dropwise to a solution of 4-bromo-N-[2-(methoxy)ethyl]benzenesulfonamide (0.5 g, 1.72 mmol) and triisopropylborate (4.8 mL, 20.89 mmol) in THF (15 mL) at −78° C. The mixture was stirred at −78° C. for 3 h and allowed to warm up to ambient temperature, stirred at ambient temperature overnight. The mixture was quenched with water (5 mL) and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 30% 2M NH3 in MeOH/CH2Cl2 to give 400 mg (89%) of [4-({[2-(methoxy)ethyl]amino}sulfonyl)phenyl]boronic acid as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.06-7.28 (m, 4H), 3.25-3.19 (m, 2H), 3.16-3.06 (m, 3H), 2.88-2.74 (m, 2H); LRMS (ESI), m/z 258 (M−H).

Workup

  1. temperatureto warm up to ambient temperature
  2. stirringstirred at ambient temperature overnight
  3. customThe mixture was quenched with water (5 mL)
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-7e8c46621b954ccc815af6fc3cc19f12
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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