Sodium triacetoxyborohydride → 4-({4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-7-carbonitrile

HRID 1519603Notes

Reaction equation

HRID 1519603 reaction equation
[CH:1]([CH:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1)=O.[N:15]1([CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:26]3[C:27](=[O:30])[O:28][CH2:29][C:25]=3[CH:24]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:30]=[C:27]1[C:26]2[CH:31]=[CH:32][C:23]([CH2:22][CH2:21][N:15]3[CH2:20][CH2:19][N:18]([CH2:1][CH:3]4[C:12]5[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=5)[O:6][CH2:5][CH2:4]4)[CH2:17][CH2:16]3)=[CH:24][C:25]=2[CH2:29][O:28]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 772307034-Formyl-3,4-dihydro-2H-chromene-7-carbonitrile

Product 1

HCID 866944804-({4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 12 mL reaction vial was added 4-formyl-3,4-dihydro-2H-chromene-7-carbonitrile (50 mg, 0.27 mmol), 5-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (66 mg, 0.27 mmol) and dichloromethane (3 mL). The solution was stirred at RT under N2 for 10 min. To above solution was added sodium tris(acetoxy) borohydride (224 mg, 1.1 mmol). The reaction was stirred at RT for 18 hours under N2, extracted with DCM, washed with brine and water. The organic phase was dried over MgSO4, filtered and purified by flash column chromatography. LC-MS (IE, m/z): 418.1 [M+1]+. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.84 (1H, d, J=7.8 Hz), 7.38 (1H, d, J=7.8 Hz), 7.32 (2H, m), 7.11 (1H, dxd, J=8.0 Hz, J=1.6 Hz), 7.08 (1H, d, J=1.6 Hz), 5.60 (2H, s), 4.4 (2H, m), 3.0 (4H, m), 2.4-2.8 (10H, m), 2.0 (2H, m). (0.092 μM)

Workup

  1. customTo a 12 mL reaction
  2. stirringThe reaction was stirred at RT for 18 hours under N2
  3. extractionextracted with DCM
  4. washwashed with brine and water
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-3cd156967d6d46e88a5fa1feebda31e8
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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