Water → HCID 178514936, compound

HRID 2243373Notes

Reaction equation

HRID 2243373 reaction equation
[F:1][C:2]1[C:24]([O:25]C)=[CH:23][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[O:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[C:24]([OH:25])=[CH:23][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[O:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 178486893HCID 178486893, compound

Product 1

HCID 178514936HCID 178514936, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The procedure used in stage 1 of Example 230 is followed. In a 50 ml round-bottomed flask under argon, dissolve 1.07 g of 4-(5-fluoro-6-methoxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one, obtained in stage 3 of Example 268, in 20 ml of dichloromethane, cooled to 0° C. and add 7.8 ml of a molar solution of boron tribromide in dichloromethane. After stirring for 20 hours, the reaction mixture is poured into water, and the insoluble material is drained, washed with water and then dried. After purification by formation of a paste with diisopropyl ether, in this way we obtain 914 mg of 4-(5-fluoro-6-hydroxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one, in the form of a brown powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. washwashed with water
  2. customdried
  3. customAfter purification by formation of a paste with diisopropyl ether

Sources & evidence

ORD record
ord-48bd727214fd47eb8f037c03c4bb1299
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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