Cesium carbonate → HCID 69671102, compound

HRID 626790Notes

Reaction equation

HRID 626790 reaction equation
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[N:10]=[C:6]2[C:5]([F:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:18]1[C:11]([N:9]2[CH:8]=[C:7]3[C:2]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:3][CH:4]=[C:5]([F:20])[C:6]3=[N:10]2)=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 5728526-Methylpyrimidin-4-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86697078HCID 86697078, compound

Product 1

HCID 69671102HCID 69671102, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-fluorobenzonitrile (85 mg, 0.25 mmol), 4-amino-6-methylpyrimidine (31 mg, 0.28 mmol), Pd2(dba)3 (12 mg, 0.013 mmol), Xantphos (15 mg, 0.026 mmol) and cesium carbonate (166 mg, 0.51 mmol) in dioxane (1.8 mL) was de-gassed and purged with nitrogen and the reaction mixture was heated at 150° C. in a sealed vial for 30 minutes. The resultant mixture was diluted with dioxane and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography (10-100% ethyl acetate in cyclohexane) to afford the title compound as a brown solid (47 mg, 51% yield). LCMS (Method C): RT=2.25 min, m/z: 364 [M+H+].

Workup

  1. customwas de-gassed
  2. custompurged with nitrogen
  3. additionThe resultant mixture was diluted with dioxane
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel flash chromatography (10-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-4162488e2460430d8e26f781b52d846b
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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