4,5-Dimethyl-1,2-phenylenediamine → HCID 135804678, compound

HRID 2064603Notes

Reaction equation

HRID 2064603 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[CH3:8].[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([CH:21]=O)=[N:15][NH:16]2>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[NH:9][C:21]([C:14]3[C:13]4[C:17](=[CH:18][CH:19]=[CH:20][C:12]=4[F:11])[NH:16][N:15]=3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 178520028HCID 178520028, compound

Product 1

HCID 135804678HCID 135804678, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4,5-dimethylbenzene-1,2-diamine (70 mg) and 4-fluoro-1H-indazole-3-carbaldehyde [80 mg, Reference Example 20(b)] in dimethylformamide (8 ml) was heated to 120° C. for 30 minutes and then at 100° C. for 16 hours. The reaction mixture was cooled, then diluted with ethyl acetate and then washed five times with brine. The organic phase was dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of 40/60 petrol and ethyl acetate (1:5, v/v) to give 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4-fluoro-1H-indazole (104 mg) as a light brown solid. MS: 281 (M+H)+. HPLC (METHOD B1): RT=10.08 minutes.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed five times with brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of 40/60 petrol and ethyl acetate (1:5

Sources & evidence

ORD record
ord-eb7b66c510ed46f3bb073422f21d8a05
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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