Cesium carbonate → HCID 117652491, compound

HRID 1500829Notes

Reaction equation

HRID 1500829 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](B(O)O)=[C:4]([O:12][CH3:13])[CH:3]=1.[Br:14][C:15]1[CH:16]=[C:17]2[C:23](I)=[CH:22][N:21]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:18]2=[N:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:14][C:15]1[CH:16]=[C:17]2[C:23]([C:5]3[CH:6]=[C:7]([CH3:8])[C:2]([F:1])=[CH:3][C:4]=3[O:12][CH3:13])=[CH:22][N:21]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:26])=[O:27])[C:18]2=[N:19][CH:20]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 54758895(4-Fluoro-2-methoxy-5-methylphenyl)boronic acid

Product 1

HCID 117652491HCID 117652491, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of (4-fluoro-2-methoxy-5-methylphenyl)boronic acid (100 mg, 0.5434 mmol) 134 and 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine 78 (259.23 mg, 0.5434 mmol) in acetonitrile was added cesium carbonate (356.4 mg, 1.86 mmol). The reaction was degassed and purged with nitrogen for 10 min and Pd(dppf)Cl2 (22.17 mg, 0.0217 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90° C. under sealed condition for overnight. The reaction mixture was allowed to cool to room temperature, diluted with chloroform. The organic layer was filtered through celite plug and concentrated to get the crude compound 135. The crude was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 5% ethyl acetate in hexane as half white solid 5-bromo-3-(4-fluoro-2-methoxy-5-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine 135.

Workup

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 10 min
  3. customThe reaction was degassed
  4. custompurged with nitrogen for another 10 min
  5. customunder sealed condition for overnight
  6. temperatureto cool to room temperature
  7. additiondiluted with chloroform
  8. filtrationThe organic layer was filtered through celite plug
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5532b28308e44c2ca47ac74731fc3f19
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

Loading…