Cesium carbonate → HCID 86696909, compound

HRID 1399998Notes

Reaction equation

HRID 1399998 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:23]=[N:24][C:25]([C:28]([OH:31])([CH3:30])[CH3:29])=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].BrC1C=NC(C23OC2[CH2:43][O:42][CH2:41]C3)=NC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[CH:30]12[O:31][C:28]1([C:25]1[N:26]=[CH:27][C:22]([C:13]3[CH:14]=[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)[C:9]4[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=4[CH:12]=3)=[CH:23][N:24]=1)[CH2:29][CH2:43][O:42][CH2:41]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 71726538HCID 71726538, compoundHCID 86696908HCID 86696908, compound

Product 1

HCID 86696909HCID 86696909, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Intermediate 1 (29 mg, 0.085 mmol), ii (20 mg, 78 mmol), Cs2CO3 (55 mg 0.17 mmol) and Pd(Ph3)2Cl2 (3 mg, 4 mmol) were dissolved in 1,4-dioxane:H2O (10:1, 10 mL). The mixture was degassed with a stream of N2 for 10 min, then heated in a microwave reactor at 80° C. for 1 h. The reaction was concentrated in vacuo, re-dissolved in a minimum quantity of DCM and purified by chromatography on silica (0-10% DCM-MeOH) yielding iii (23 mg 57%). MS: 475.0, [M+H]+.

Workup

  1. customThe mixture was degassed with a stream of N2 for 10 min
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionre-dissolved in a minimum quantity of DCM
  4. custompurified by chromatography on silica (0-10% DCM-MeOH)

Sources & evidence

ORD record
ord-61ae7bc3ea474bf6945cac4f74cb9451
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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