Ethyl Bromide → HCID 11743889, compound

HRID 1453987Notes

Reaction equation

HRID 1453987 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:17]([C:18]#[N:19])=[CH:16][O:15][CH:14]3[C:20]4[C:24](=[CH:25][CH:26]=[C:13]23)[N:23]=[CH:22][CH:21]=4)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].Br[CH2:28][CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:17]([C:18]#[N:19])=[CH:16][O:15][C:14]3[C:20]4[CH:21]=[CH:22][N:23]([CH2:28][CH3:29])[C:24]=4[CH:25]=[CH:26][C:13]2=3)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 6332Ethyl Bromide2×HCID 10796Cesium carbonateHCID 69001380HCID 69001380, compound

Product 1

HCID 11743889HCID 11743889, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-indolo[4,5-b]pyran (50 mg, 0.122 mmol), bromoethane (50 μL, 0.670 mmol) and cesium carbonate (122 mg, 0.375 mmol) in anhydrous THF (2 mL) was stirred at 60° C. in a sealed tube. After 22 h, additional bromoethane (100 μL, 1.34 mmol) was added and the reaction was continued for additional 43 h. The reaction mixture was diluted with EtOAc (20 mL). The insoluble material was filtered, and washed with EtOAc (30 mL). The EtOAc solution were combined, washed with brine (2×5 mL), dried over MgSO4, and evaporated to yield a light yellow solid. The crude product was purified by column chromatography (silica gel, EtOAc:hexanes, 1:3) to yield 27 mg (51%) of the product as an off-white solid. 1H NMR (CDCl3) 7.44 (d, J=0.9 Hz, 1H), 7.14 (d, J=3.3 Hz, 1H), 7.07 (dd, J=0.6, 8.4 Hz, 1H), 6.96 (d, J=1.8 Hz, 1H), 6.77 (d, J=1.8 Hz, 1H), 6.70 (d, J=8.4 Hz, 1H), 6.59 (dd, J=0.9, 3.3 Hz, 1H), 4.81 (s, 1H), 4.15 (q, J=7.2 Hz, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 1.46 (t, J =7.2 Hz, 3H).

Workup

  1. waitthe reaction was continued for additional 43 h
  2. filtrationThe insoluble material was filtered
  3. washwashed with EtOAc (30 mL)
  4. washwashed with brine (2×5 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto yield a light yellow solid
  8. customThe crude product was purified by column chromatography (silica gel, EtOAc:hexanes, 1:3)

Sources & evidence

ORD record
ord-0cc245e639524e598f913840fa9211a1
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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