Sodium triacetoxyborohydride → HCID 68071887, compound

HRID 1519631Notes

Reaction equation

HRID 1519631 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[O:19]=[C:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]=O)=[CH:28][C:23]=2[CH2:22][O:21]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:30][CH2:29][C:27]3[CH:26]=[CH:25][C:24]4[C:20](=[O:19])[O:21][CH2:22][C:23]=4[CH:28]=3)[CH2:17][CH2:18]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67513198HCID 67513198, compoundHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 68071887HCID 68071887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(methylthio)-4-(2-piperazin-1-ylethyl)benzonitrile (0.69 mmol) in 20 mL of DCM was added (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (180 mg, 1.03 mmol) and NaBH(OAc)3 (580 mg, 2.8 mmol), and the mixture was stirred at room temperature overnight. The reaction was diluted with DCM, and washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 2-(methylthio)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.82 (d, J=8.6 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.33˜7.37 (m, 2H), 7.16 (s, 1H), 7.02˜7.05 (m, 1H), 5.27 (s, 2H), 2.49˜3.01 (m, 19H). (0.55 μM)

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-ef367ad14fd14a0c962cb795a02c6b48
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…