2-(4-bromobutylamino)-1H-indene-1,3(2H)-dione → Methyl 2-(2-bromo-5-(1-(4-(1,3-dioxo-2,3-dihydro-1H-inden-2-ylamino)butyl)-2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl)acetate

HRID 453616Notes

Reaction equation

HRID 453616 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:9]=[C:8]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[NH:18]3)=[CH:14][CH:13]=2)=[O:11])[S:7][C:6]=1[Br:27].Br[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][CH:35]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]1=[O:45]>CC#N>[Br:27][C:6]1[S:7][C:8]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:18]3[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][CH:35]3[C:36](=[O:45])[C:37]4[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:43]3=[O:44])=[CH:14][CH:13]=2)=[O:11])=[CH:9][C:5]=1[CH2:4][C:3]([O:2][CH3:1])=[O:28]

Participants

4

Reactant 2

HCID 684945492-(4-bromobutylamino)-1H-indene-1,3(2H)-dioneHCID 86664845Methyl (2-bromo-5-(2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate

Product 1

HCID 68493100Methyl 2-(2-bromo-5-(1-(4-(1,3-dioxo-2,3-dihydro-1H-inden-2-ylamino)butyl)-2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl)acetateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 453 mg (1 mmol) of methyl-(2-bromo-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl)acetate in 10 mL of anhydrous CH3CN was added 1.25 g of CsF-Celite under N2, and then followed by 295 mg (1 mmol) 2-(4-bromobutylamino)-1H-indene-1,3(2H)-dione. The resulting mixture was refluxed for 5 h. The mixture was filtered and washed with CH3CN (5 mL×3), the filtrate was evaporated under reduced pressure, and the residue was purified by MPLC (EtOAc/Hex 1:4) to give 280 mg product as a yellow solid (yield 42%).

Workup

  1. temperatureThe resulting mixture was refluxed for 5 h
  2. filtrationThe mixture was filtered
  3. washwashed with CH3CN (5 mL×3)
  4. customthe filtrate was evaporated under reduced pressure
  5. customthe residue was purified by MPLC (EtOAc/Hex 1:4)

Sources & evidence

ORD record
ord-66cfbd53d9b7402697a105a047c71b5b
Source dataset
uspto-grants-2013_07
Patent number
US08492428B2

Reaction notes

Loading…