Sodium triacetoxyborohydride → HCID 86694486, compound

HRID 1519640Notes

Reaction equation

HRID 1519640 reaction equation
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:11]=[C:10]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[O:21]=[C:22]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][CH:32]=O)=[CH:30][C:25]=2[CH2:24][O:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:11]=[C:10]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:32][CH2:31][C:29]3[CH:28]=[CH:27][C:26]4[C:22](=[O:21])[O:23][CH2:24][C:25]=4[CH:30]=3)[CH2:16][CH2:15]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67513243HCID 67513243, compoundHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 86694486HCID 86694486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude 2-(difluoromethoxy)-4-(2-piperazin-1-ylethyl)benzonitrile (15 mg, 0.05 mmol), (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (18 mg, 0.1 mmol) and NaBH(OAc)3 (100 mg, 0.47 mmol) in 10 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM, washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford 2-(difluoromethoxy)-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 7.82 (d, J=7.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 7.33˜7.36 (m, 2H), 7.13˜7.20 (m, 2H), 6.33 (t, J=71.2 Hz, 1H), 5.26 (s, 2H), 2.99˜3.08 (m, 2H), 2.87˜2.90 (m, 2H), 2.62˜2.84 (m, 12H). (0.15 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-d349c1c0c5714818a4230557993b0308
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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