Sodium hydride → HCID 67327191, compound

HRID 1255646Notes

Reaction equation

HRID 1255646 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[CH:5][C:4]=1[OH:20])#[N:2].[H-].[Na+].[CH:23]1(I)[CH2:27][CH2:26][CH2:25][CH2:24]1>C1COCC1.CN(C=O)C>[CH:23]1([O:20][C:4]2[CH:5]=[C:6]([O:7][C:8]3[CH:9]=[CH:10][C:11]4[B:15]([OH:16])[O:14][CH2:13][C:12]=4[CH:17]=3)[CH:18]=[CH:19][C:3]=2[C:1]#[N:2])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 73784IodocyclopentaneHCID 67327262HCID 67327262, compound

Product 1

HCID 67327191HCID 67327191, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzonitrile (D10) (200 mg, 0.75 mmol) in THF (50 mL) and DMF (20 mL) was added NaH (47 mg, 95%, 1.87 mmol) portion- wise. The mixture was stirred at room temperature for 5 minutes, followed by the slow addition of cyclopentyl iodide (0.26 mL, 2.25 mmol). The reaction was stirred at room temperature for 24 hours. After the reaction, all volatile components were evaporated under vacuum. The residue was purified using silica gel column chromatography, eluting with 25% EtOAc/hexane, afforded 36 mg of the title compound in 12.6% yield. 1H NMR 400 MHz (DMSO-d6) δ: 9.23 (s, 1H), 7.78 (d, J=7.8 Hz, 1H) 7.69 (d, J=8.6 Hz, 1H), 7.17 (s, 1H), 7.10 (dd, J=2.0, 8.2 Hz, 1H), 6.90 (d, J=2.3 Hz, 1H), 6.56 (dd, J=1.9, 8.6 Hz, 1H), 4.96 (s, 2H), 4.95 (t, J=5.8 Hz, 1H), 1.95-1.55 (m, 8H); MS (ES) m/z: 336 (M+H)+; HPLC purity: 99.15% (220 nm), 99.62% (MaxPlot).

Workup

  1. stirringThe reaction was stirred at room temperature for 24 hours
  2. customAfter the reaction
  3. customall volatile components were evaporated under vacuum
  4. customThe residue was purified
  5. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-369b3084637848009e1e7ce79f0dba26
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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