Cesium carbonate → HCID 87449801, compound

HRID 390717Notes

Reaction equation

HRID 390717 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8].ClC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:35][C:36]1[S:37][C:38](Br)=[CH:39][CH:40]=1.[OH-].[NH4+].O>CN1CCCC1=O>[Br:35][C:36]1[S:37][C:38]([N:3]2[CH:4]=[CH:5][S:1]/[C:2]/2=[N:6]\[C:7]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:8])=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 184532,5-DibromothiopheneHCID 778655-Chloro-1,10-phenanthrolineHCID 86589665Water ammonium hydroxideHCID 86631924N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide

Product 1

HCID 87449801HCID 87449801, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

In a 4 mL vial charged with a stir bar, N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide (69 mg, 0.35 mmol, Example 32A) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (35 mg, 0.07 mmol), 5-chloro-1,10-phenanthroline (30 mg, 0.14 mmol) and cesium carbonate (125 mg, 0.39 mmol). A loose cap with a septum was placed on the vial and then the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. 2,5-Dibromothiophene (102 mg, 0.42 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then 1 mL of a solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound.

Workup

  1. additionIn a 4 mL vial charged with a stir bar
  2. customA loose cap with a septum
  3. customThe solid mixture was purged with nitrogen gas a couple of times
  4. additionwas added to the mixture
  5. customThe vial was capped
  6. customplaced on a heater/stirrer
  7. filtrationThe reaction was filtered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c8f8303d751949e197e2bf195d0d7d7b
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Reaction notes

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