HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cesium carbonate → (+,-) Cis Propane-2-sulfonic Acid [2-(4'-cyano-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989498
Notes
Print preview

Reaction equation

HRID 989498 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([C@H:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)#[N:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343264-Cyanophenylboronic acidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103239(+,-) Cis Propane-2-sulfonic Acid [2-(4'-cyano-biphenyl-4-yl)-cyclopentyl]-amideYield 9%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
85 °C

Procedure

(+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (150 mg, 0.38 mmol, prepared in example 17) was treated with 4-cyanophenyl boronic acid (56 mg, 0.38 mmol), palladium tetrakis triphenylphosphine (22 mg, 0.02 mmol) and cesium carbonate (150 mg, 0.46) under nitrogen in 10 mL of degassed dioxane. The reaction was heated to 85° C. and stirred overnight. The reaction was concentrated in vacuo and purified by radial chromatography eluting with 30:70 ethyl acetate:hexanes to give 12 mg (9%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by radial chromatography
  3. washeluting with 30:70 ethyl acetate

Sources & evidence

ORD record
ord-fd44af02e30c4fd7ad0d9bdc500d0099
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06639107B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes