Acetonitrile → HCID 117652417, compound

HRID 1500830Notes

Reaction equation

HRID 1500830 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[CH:13][C:12]=3[O:19][CH3:20])=[CH:9][N:8]([S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:37](#[N:39])[CH3:38]>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]>[F:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:4]4[CH:38]=[C:37]([CH:7]=[CH:2][CH:3]=4)[NH2:39])[CH:3]=3)[N:8]([S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:22])=[O:23])[CH:9]=2)=[C:12]([O:19][CH3:20])[CH:13]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 117652491HCID 117652491, compound

Product 1

HCID 117652417HCID 117652417, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
90 °C

Procedure

A solution of 5-bromo-3-(4-fluoro-2-methoxy-5-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine 135 (250 mg, 0.5122 mmol) and 23 (145.9 mg, 0.655 mmol) in acetonitrile was added cesium carbonate (336.03 mg, 1.024 mmol). The reaction was degassed and purged with nitrogen for 10 min and Pd(dppf)Cl2 (20.8 mg, 0.02561 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 136. 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 3-(3-(4-fluoro-2-methoxy-5-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline 136.

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-bcf4753493aa4708b3ebc754ea30598f
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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