Trimethyl borate → 1H-Indole-1-carboxylic acid, 2-borono-5-[(4-methyl-1-piperazinyl)sulfonyl]-, 1-(1,1-dimethylethyl) ester

HRID 1375431Notes

Reaction equation

HRID 1375431 reaction equation
C([Li])(C)(C)C.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([S:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=[CH:19]3)(=[O:15])=[O:14])[CH2:9][CH2:8]1.[B:32](OC)([O:35]C)[O:33]C>CCCCC.C1COCC1>[C:28]([O:27][C:25]([N:21]1[C:22]2[C:18](=[CH:17][C:16]([S:13]([N:10]3[CH2:9][CH2:8][N:7]([CH3:6])[CH2:12][CH2:11]3)(=[O:15])=[O:14])=[CH:24][CH:23]=2)[CH:19]=[C:20]1[B:32]([OH:35])[OH:33])=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 58787188tert-Butyl 5-((4-methylpiperazin-1-yl)sulfonyl)-1H-indole-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 573504271H-Indole-1-carboxylic acid, 2-borono-5-[(4-methyl-1-piperazinyl)sulfonyl]-, 1-(1,1-dimethylethyl) ester

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyllithium (1.7 M, 6.20 mL, 10.5 mmol, 2.00 equiv) in pentane was added to a solution of tert-butyl 5-[(4-methylpiperazin-1-yl) sulfonyl]-1H-indole-1-carboxylate (1-9, 2.00 g, 5.27 mmol, 1 equiv) in THF (150 mL) at −78° C. The resulting orange-colored reaction mixture was stirred at −78° C. for 1.5 hours before trimethyl borate (1.50 mL, 13.2 mmol, 2.50 equiv) was added. The mixture was warmed to 0° C. where it was stirred for 20 minutes, then 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-methylpiperazin-1-yl)sulfonyl]-1H-indol-2-ylboronic acid (1-10) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.12 (d, 1H, J=8.8 Hz), 8.02 (d, 1H, J=1.6 Hz), 7.71 (d, 7.71 (dd, 1H, J=8.6, 1.8 Hz), 7.49 (s, 1H), 3.05 (br m, 4H), 2.48 (br m, 4H), 2.25 (s, 3H), 1.75 (s, 9H).

Workup

  1. additionwas added
  2. custompartitioned 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-5569e22b3007499ba2cb8df6c34b701f
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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