N-(4-Bromobutyl)phthalimide → Methyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2-phenyl-1H-indole-6-carbonyl)-thiophene-3-yl)acetate

HRID 1952502Notes

Reaction equation

HRID 1952502 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].Br[CH2:30][CH2:31][CH2:32][CH2:33][N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44]>CC#N>[Br:1][C:2]1[S:3][C:4]([C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:20]3[CH2:30][CH2:31][CH2:32][CH2:33][N:34]3[C:38](=[O:39])[C:37]4[C:36](=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:35]3=[O:44])=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 93575N-(4-Bromobutyl)phthalimideHCID 86664845Methyl (2-bromo-5-(2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate

Product 1

HCID 67495985Methyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2-phenyl-1H-indole-6-carbonyl)-thiophene-3-yl)acetateYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4 (45 mg, 0.10 mmol) in anhydrous CH3CN (5 mL) was added CsF-Celite (125 mg) under N2, followed by addition of N-(4-bromobutyl)-phthalimide (28 mg, 0.10 mmol). The resulting mixture was refluxed for five hours, cooled to room temperature, and filtered. The filtrate was evaporated in vacuo. MPLC purification (Hex:EtOAc/4:1) of the residue gave 5 as a yellow solid (28 mg, 43%). 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.74 (m, 6H), 7.59 (s, 1H), 7.47 (m, 5H), 6.60 (s, 1H), 4.32 (t, J=7.2 Hz, 2H), 3.73 (s, 3H), 3.71 (s, 2H), 3.52 (t, J=6.8 Hz, 2H), 1.72 (m, 2H), and 1.51 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 187.3, 170.4, 168.5, 145.2, 144.3, 136.8, 135.6, 134.9, 134.2, 134.1, 132.5, 132.1, 130.7, 129.5, 129.0, 128.8, 123.5, 123.4, 121.5, 120.6, 112.5, 103.1, 52.5, 43.7, 37.3, 35.1, 27.4, and 25.8.

Workup

  1. temperatureThe resulting mixture was refluxed for five hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. customMPLC purification (Hex:EtOAc/4:1) of the residue

Sources & evidence

ORD record
ord-167b8956e6f6470e821595d10ec2174d
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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