Bromoacetonitrile → HCID 24775759, compound

HRID 1159811Notes

Reaction equation

HRID 1159811 reaction equation
[OH:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.Br[CH2:35][C:36]#[N:37].[OH-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:14]1([S:11]([N:7]2[C:8]3[C:4](=[C:3]([CH2:20][N:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)[C:2]([O:1][CH2:35][C:36]#[N:37])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:12])=[O:13])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 14798Sodium HydroxideHCID 86618251HCID 86618251, compound2×

Product 1

HCID 24775759HCID 24775759, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 4-{[5-hydroxy-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate (45 mg, 0.10 mmol; Intermediate 64) in dry DCM (2 mL) was added bromoacetonitrile, 57 mg (0.48 mmol), tetrabutylammonium hydrogensulphate, 8 mg (0.02 mmol), 2M NaOH (1 mL) and the two phase system was vigorously stirred at room temperature over night. The organic phase was separated and the aqueous phase was washed once with water. The solvent from the combined organic phases was removed at reduced pressure and the residue was purified on a on a preparative HPLC, method B, to yield 2.9 mg (7%) of the target compound as a light brown oil. MS (ESI+) for C21H22N4O3S m/z 411 (M+H)+.

Workup

  1. customThe organic phase was separated
  2. washthe aqueous phase was washed once with water
  3. customThe solvent from the combined organic phases was removed at reduced pressure
  4. customthe residue was purified on a on a preparative HPLC, method B

Sources & evidence

ORD record
ord-a6222f6a08ce435cbb9849f69da1d87f
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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