Boron trifluoride etherate → {1-(tert-Butoxycarbonyl)-5-[4-(tert-butoxycarbonyl)piperazine-1-sulfonyl]-1H-indol-2-yl}boronic acid

HRID 1375434Notes

Reaction equation

HRID 1375434 reaction equation
C([Li])(C)(C)C.[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[B:38](OC)([O:41]C)[O:39]C.B(F)(F)F.CCOCC>CCCCC.C1COCC1>[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[B:38]([OH:41])[OH:39])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8470Trimethyl borateHCID 21963096tert-Butyl 5-[4-(tert-butoxycarbonyl)piperazine-1-sulfonyl]-1H-indole-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 21963088{1-(tert-Butoxycarbonyl)-5-[4-(tert-butoxycarbonyl)piperazine-1-sulfonyl]-1H-indol-2-yl}boronic acid

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyllithium (1.7 M, 4.55 mL, 7.73 mmol, 2.00 equiv) in pentane was added to a solution of tert-butyl 5-{[4-(tert-butoxycarbonyl) piperazin-1-yl]sulfonyl}-1H-indole-1-carboxylate (2-2, 1.80 g, 3.87 mmol, 1 equiv) in THF (100 mL) at −78° C. The resulting orange-colored reaction mixture was stirred at −78° C. for 1.5 hour before trimethyl borate (1.10 mL, 9.66 mmol, 2.50 equiv) was added. The mixture was warmed to 0° C. and stirred for 20 minutes. Boron trifluoride diethyl etherate (1.20 mL, 9.66 mmol, 2.50 equiv) was then added, and the resulting mixture was partitioned between aqueous half-saturated ammonium chloride solution (200 mL) and EtOAc (2×200 mL). The organic layer was dried over sodium sulfate and concentrated to give 1-(tert-butoxycarbonyl)-5-{[4-(tert-butoxycarbonyl) piperazin-1-yl]sulfonyl}-1H-indol-2-ylboronic acid (2-3) as a tan solid. LCMS [M+H]+ observed=510.3; calculated=510.4.

Workup

  1. additionwas added
  2. customthe resulting mixture was partitioned between aqueous half-saturated ammonium chloride solution (200 mL) and EtOAc (2×200 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0685b766e3304e5495d2a0a59a198b60
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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