Ethyl Acrylate → HCID 68636008, compound

HRID 1177647Notes

Reaction equation

HRID 1177647 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:11][C:12]4[C:17]([N:18]=3)=[CH:16][CH:15]=[C:14]([C:19]3([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:21][CH2:20]3)[N:13]=4)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:28]([O:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:22]1([C:19]2([C:14]3[N:13]=[C:12]4[S:11][C:10]([C:6]5[CH:5]=[C:4]6[C:9](=[CH:8][CH:7]=5)[N:1]([CH2:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:34])[CH:2]=[CH:3]6)=[N:18][C:17]4=[CH:16][CH:15]=3)[CH2:20][CH2:21]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 10796Cesium carbonateHCID 59174911HCID 59174911, compound

Product 1

HCID 68636008HCID 68636008, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-(1H-indol-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (90 mg, 0.245 mmol) was added acetonitrile (2.4 mL), ethylacrylate (80 μl, 735 μmol), and cesium carbonate (160 mg, 0.490 mmol) before it was stirred at ambient temp. for 3 h; the reaction mixture was quenched with 2 N HCl, concentrated, and was diluted with 75 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 1 time with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give ethyl 3-(5-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-1H-indol-1-yl)propanoate.

Workup

  1. customthe reaction mixture was quenched with 2 N HCl
  2. concentrationconcentrated
  3. additionwas diluted with 75 mL of EtOAc
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed 1 time with 50 mL of water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-c6e45f827926477d934f3180f6aaa8f5
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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