4-Aminobenzonitrile → HCID 57693596, compound

HRID 1516823Notes

Reaction equation

HRID 1516823 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:12]([N:19]1[C:23]2[N:24]=[C:25](F)[N:26]=[C:27]([O:28][C:29]3[C:36]([CH3:37])=[CH:35][C:32]([C:33]#[N:34])=[CH:31][C:30]=3[CH3:38])[C:22]=2[CH:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1C=CC=CC1=O>[CH2:12]([N:19]1[C:23]2[N:24]=[C:25]([NH:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[N:26]=[C:27]([O:28][C:29]3[C:30]([CH3:38])=[CH:31][C:32]([C:33]#[N:34])=[CH:35][C:36]=3[CH3:37])[C:22]=2[CH:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 24758Sodium hydrideHCID 576935774-(7-benzyl-2-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile

Product 1

HCID 57693596HCID 57693596, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 127551-Methyl-2(1H)-pyridinoneSolvent2×

Procedure

To a solution of 4-aminobenzonitrile (54 mg, 0.46 mmol) in 1-methyl-2-pyridone (1 mL) was added NaH (18 mg, 0.46 mmol). The reaction mixture was stirred at room temperature for 15 min and a solution of 4-(7-benzyl-2-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile (34 mg, 0.091 mmol) in 1-methyl-2-pyridone (1 mL) was added to the mixture. The mixture was stirred at room temperature for 1 h, poured into ice water and extracted with EtOAc (2×20 mL). The combined organic solution was washed with H2O (20 mL) and brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=75:25) yielded 28 mg (65%) of 4-[7-benzyl-2-(4-cyano-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-3,5-dimethyl-benzonitrile.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic solution was washed with H2O (20 mL) and brine (20 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-829f1e5545014cbfbbe96dc21a6f3d41
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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