Dimethylformamide → HCID 136387224, compound

HRID 1396560Notes

Reaction equation

HRID 1396560 reaction equation
Br.[NH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:21])[N:10]=[C:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([OH:19])=[C:14](Br)[CH:13]=3)[C:6]2=[CH:5][N:4]=1.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].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].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.[Fe+2]>[NH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:21])[N:10]=[C:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([OH:19])=[C:14]([CH:13]=3)[C:22]#[N:23])[C:6]2=[CH:5][N:4]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 136350338HCID 136350338, compound

Product 1

HCID 136387224HCID 136387224, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
180 °C

Procedure

4-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-bromo-6-fluoro-phenol hydrobromide (Example 42a) (0.07 g, 0.167 mmol), Zn(CN)2 (0.020 g, 0.167 mmol), Pd2(dba)3 (0.076 g, 0.08 mmol) and DPPF (0.092 g, 0.167 mmol) are dissolved in DMF (2.5 ml) and heated to 180° C. for 40 minutes. The reaction mixture is flitered through Celite® (filter agent) washing with MeOH, the filtrate is concentrated in vacuo and purification of the resulting residue is by preparative HPLC (water/acetonitrile, 0.1% TFA) affords the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture is flitered through Celite® (filter agent)
  2. washwashing with MeOH
  3. concentrationthe filtrate is concentrated in vacuo and purification of the resulting residue

Sources & evidence

ORD record
ord-e63e99c0095c42819310059f5d075e49
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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