Sodium triacetoxyborohydride → HCID 56970864, compound

HRID 1519644Notes

Reaction equation

HRID 1519644 reaction equation
[CH:1]1([O:4][C:5]2[CH:12]=[C:11]([CH2:13][CH:14]=O)[CH:10]=[CH:9][C:6]=2[C:7]#[N:8])[CH2:3][CH2:2]1.[N:16]1([CH2:22][CH2:23][C:24]2[CH:33]=[CH:32][C:27]3[C:28](=[O:31])[O:29][CH2:30][C:26]=3[CH:25]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH:1]1([O:4][C:5]2[CH:12]=[C:11]([CH2:13][CH2:14][N:19]3[CH2:20][CH2:21][N:16]([CH2:22][CH2:23][C:24]4[CH:33]=[CH:32][C:27]5[C:28](=[O:31])[O:29][CH2:30][C:26]=5[CH:25]=4)[CH2:17][CH2:18]3)[CH:10]=[CH:9][C:6]=2[C:7]#[N:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 86694487HCID 86694487, compound

Product 1

HCID 56970864HCID 56970864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude 2-(cyclopropyloxy)-4-(2-oxoethyl)benzonitrile (80 mg, 0.4 mmol), 5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one (150 mg, 0.6 mmol) and NaBH(OAc)3 (400 mg, 2 mmol) in 10 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford 2-(cyclopropyloxy)-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 7.77 (d, J=7.8 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.11 (s, 1H), 6.78˜6.80 (m, 1H), 5.22 (s, 2H), 2.42˜2.93 (m, 17H), 0.77˜0.80 (m, 4H). (0.28 μM)

Workup

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

Sources & evidence

ORD record
ord-dbefc149f9a84692bdfde709030083ee
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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