Sodium triacetoxyborohydride → HCID 117599536, compound

HRID 1466160Notes

Reaction equation

HRID 1466160 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]2=[O:18])=[CH:6][C:3]=1[C:4]#[N:5].[F:19][CH:20]([C:23]1[CH:32]=[CH:31][C:26]2[C:27](=[O:30])[O:28][CH2:29][C:25]=2[CH:24]=1)[CH:21]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:21][CH:20]([F:19])[C:23]3[CH:32]=[CH:31][C:26]4[C:27](=[O:30])[O:28][CH2:29][C:25]=4[CH:24]=3)[CH2:14][C:13]2=[O:18])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 89524959HCID 89524959, compoundHCID 117599366HCID 117599366, compound

Product 1

HCID 117599536HCID 117599536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with 2-Fluoro-5-[2-(2-oxopiperazin-1-yl)ethyl]benzonitrile (53 mg, 0.25 mmol) and Fluoro(1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (20 mg, 0.10 mmol) was added NaBH(OAc)3 (153 mg, 0.72 mmol). The mixture was stirred at RT for 12 hours. Then the reaction was diluted with DCM (120 mL), washed with brine (15 mL), dried over Na2SO4 and concentrated. The residue was purified with prep-TLC (MeOH/DCM=1:15) to obtain the title product. 1H-NMR (400 MHz, MeOD) δ ppm 7.88 (d, J=8.0 Hz, 1H), 7.55-7.65 (m, 4H), 7.25 (t, J=9.0 Hz, 1H), 5.90 (dd, J=7.6, 3.2 Hz, 1H), 5.78 (dd, J=7.6, 3.2 Hz, 1H), 5.39 (s, 2H), 3.59 (d, J=7.6, 7.0 Hz, 2H), 2.80-2.95 (m, 6H).

Workup

  1. washwashed with brine (15 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified with prep-TLC (MeOH/DCM=1:15)

Sources & evidence

ORD record
ord-02dd7251bd4843a0984eaa6f50d53952
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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