Sodium triacetoxyborohydride → 5-Fluoro-1-({2-oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1466151Notes

Reaction equation

HRID 1466151 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:7]([CH2:11][N:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]3=[O:18])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:19]#[N:20].[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.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:7]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:32][CH2:31][C:29]4[CH:28]=[CH:27][C:26]5[C:22](=[O:21])[O:23][CH2:24][C:25]=5[CH:30]=4)[CH2:14][C:13]3=[O:18])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:19]#[N:20]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 895262715-Fluoro-1-[(2-oxopiperazin-1-yl)methyl]-2,3-dihydro-1H-indene-4-carbonitrile

Product 1

HCID 1175993685-Fluoro-1-({2-oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-2,3-dihydro-1H-indene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing 5-Fluoro-1-[(2-oxopiperazin-1-yl)methyl]-2,3-dihydro-1H-indene-4-carbonitrile (5 mg, 0.018 mmol) and a stir bar was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (16 mg, 0.091 mmol), Sodium Triacetoxyborohydride (19 mg, 0.091 mmol), and DCM (1 mL). The mixture was allowed to stir at RT for 16 hours. LC-MS indicated formation of the desired product. The solvent was removed, and the residue was redissolved in MeOH (1 mL). The sample was subjected to purification by reverse phase HPLC to afford the title compound. LC-MS (IE, m/z): 434 [M+1]+.

Sources & evidence

ORD record
ord-b9925783ac864e36822290423d2a5171
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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