Cesium carbonate → HCID 67112035, compound

HRID 1177648Notes

Reaction equation

HRID 1177648 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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39]>CN(C=O)C.C(Cl)Cl>[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]([CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[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

6

Reactant 3

HCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 59174911HCID 59174911, compound

Product 1

HCID 67112035HCID 67112035, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(1H-Indol-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (80 mg, 0.218 mmol) was dissolved in DMF (1.1 mL) before cesium carbonate (156 mg, 0.479 mmol) was added and stirred at ambient temperature for 1 h; to the reaction mixture was added methyl 4-bromobutanoate (43 mg, 239 μmol) before it was stirred for 20 h at 80° C. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with water, washed 1 times with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give methyl 4-(5-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-1H-indol-1-yl)butanoate after flash chromatography. MS (ESI) m/z: Calculated: 467.2; Observed: 468.4 (M++H).

Workup

  1. additionwas added
  2. stirringwas stirred for 20 h at 80° C
  3. additionadded to a separatory funnel
  4. custompartitioned with water
  5. washwashed 1 times with 50 mL of water
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-9808feb8944946439e29365ecd9fe94e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…