Cesium carbonate → HCID 68945358, compound

HRID 1024654Notes

Reaction equation

HRID 1024654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([N:27]5[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]5[CH3:33])(=[O:26])=[O:25])[CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)=[CH:4][CH:3]=1.[NH2:49][C:50]1[CH:51]=[CH:52][C:53](Br)=[N:54][CH:55]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.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]>[NH2:49][C:50]1[CH:51]=[CH:52][C:53]([C:37]2[CH:38]=[CH:39][C:34]([C:9]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[C:13](=[O:14])[C:12]4[CH:15]=[N:16][N:17]([C:18]5[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([N:27]6[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]6[CH3:33])(=[O:25])=[O:26])[CH:19]=5)[C:11]=4[N:10]=3)=[CH:35][CH:36]=2)=[N:54][CH:55]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6428116-Bromopyridin-3-amineHCID 68944169HCID 68944169, compound

Product 1

HCID 68945358HCID 68945358, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-(4-chloro-phenyl)-1-[3-(2,5-dimethyl-pyrrole-1-sulfonyl)-phenyl]-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (0.950 g, 1.393 mmol) in N,N-dimethylformamide (40 mL) is degassed with argon for 0.5 h. Then 5-amino-2-bromopyridine (0.43 g, 2.507 mmol), cesium carbonate (0.907 g, 2.78 mmol), Pd(dppf)2Cl2 (0.122 g, 0.167 mmol) is added and the resultant mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100° C. for 6 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3×). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography (silica gel 60-120 mesh) to afford 6-[4-(5-amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-1-[3-(2,5-dimethyl-pyrrole-1-sulfonyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. customthe resultant mixture is degassed with argon for 0.5 h
  2. temperatureThe reaction mixture is cooled to rt
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by column chromatography (silica gel 60-120 mesh)

Sources & evidence

ORD record
ord-8db6b27ec1e64c51a8cb101402dc0080
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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