Sodium triacetoxyborohydride → 4-methyl-5-(1-(4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)propan-2-yl)isobenzofuran-1(3H)-one

HRID 1519649Notes

Reaction equation

HRID 1519649 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]([CH3:20])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH3:21][C:22]1[C:30]2[CH2:29][O:28][C:27](=[O:31])[C:26]=2[CH:25]=[CH:24][C:23]=1[CH2:32][CH:33]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([CH:12]([CH3:20])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:33][CH2:32][C:23]3[C:22]([CH3:21])=[C:30]4[C:26](=[CH:25][CH:24]=3)[C:27](=[O:31])[O:28][CH2:29]4)[CH2:16][CH2:15]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][O:8][C:7]2=[O:11]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 595686964-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-oneHCID 772312602-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 569710914-methyl-5-(1-(4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)propan-2-yl)isobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 12 mL reaction vial was added 4-methyl-5-[1-(piperazine-1-yl)propan-2-yl]-2-benzofuran-1(3H)-one (57 mg, 0.208 mmol), (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (47.4 mg, 0.25 mmol) and dichloromethane (5 mL). The solution was stirred at RT under N2 for 10 min. To above solution was added NaB(OAc)3H (88 mg, 0.42 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 to give desired product. LC-MS (IE, m/z): 449.4 [M+1]+. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.73 (1H, d, J=8.0 Hz), 7.67 (1H, d, J=8.0 Hz), 7.40 (1H, d, J=8.0 Hz), 7.32 (1H, d, J=8.0 Hz), 5.25 (2H, s), 5.23 (2H, s), 3.33 (1H, q), 2.90 (2H, m), 2.4-2.6 (12H, m), 2.30 (3H, s), 2.27 (3H, s), 1.28 (3H, d, J=6.6 Hz). (0.034 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-ffe0eb373f0847da95f6059c1342a4c6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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