Water → HCID 67358857, compound

HRID 2243319Notes

Reaction equation

HRID 2243319 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11]3[C:23]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16](=[O:24])[C:15]=4[CH:14]=[CH:13][CH:12]=3)[NH:8][C:7]=2[CH:25]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11]3[C:23]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16](=[O:24])[C:15]=4[CH:14]=[CH:13][CH:12]=3)[NH:8][C:7]=2[CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67359343HCID 67359343, compound

Product 1

HCID 67358857HCID 67358857, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 50-ml three-necked flask under an argon atmosphere, dissolve 700 mg of 4-(6-methoxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one, obtained in stage 2 of Example 106, in 10 ml of dichloromethane, then add dropwise 5.35 ml of a 1M solution of boron tribromide in dichloromethane and stir for 20 hours at room temperature. Pour the reaction mixture into 50 ml of water. The precipitate that forms is drained and washed with water then with toluene and finally dried. After purification by silica gel flash chromatography, eluting with a mixture of dichloromethane and methanol (90-10 by volume), we obtain 363 mg of 4-(6-hydroxy-1H-benzimidazol-2-yl)-fluoren-9-one, in the form of a brown powder, with the following characteristics:

Workup

  1. washwashed with water
  2. dry with materialwith toluene and finally dried
  3. customAfter purification by silica gel flash chromatography
  4. washeluting with a mixture of dichloromethane and methanol (90-10 by volume), we

Sources & evidence

ORD record
ord-6e3d5933d5784b78ad4d84c67c82076a
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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