Ethyl Acetate → 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-indazole

HRID 2064602Notes

Reaction equation

HRID 2064602 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[CH3:8].[NH:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([C:20](O)=O)=[N:12]1.C(OCC)(=O)C>CCCCCC>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[NH:9][C:20]([C:13]3[C:14]4[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=4[NH:11][N:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 6488524,5,6,7-Tetrahydro-1H-indazole-3-carboxylic acid

Product 1

HCID 1358046153-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-indazoleYield 17%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4,5-Dimethylbenzene-1,2-diamine (90 mg) and 4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid [110 mg, Reference Example 17(a)] were mixed in a glass vial then subjected to microwave radiation (900 W, domestic oven) twice for two minutes. The resulting solid was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (85:15, v/v) to give 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-indazole (30 mg) as a pale brown solid. LC-MS (METHOD B): RT=2.28 minutes; 267 (M+H)+.

Sources & evidence

ORD record
ord-30dcaf856fae43bd8758c69eea8f3f51
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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