Water → HCID 178519267, compound

HRID 428630Notes

Reaction equation

HRID 428630 reaction equation
B(Br)(Br)Br.[NH:5]1[CH:9]=[C:8]([CH2:10][CH:11]2[C:19]3[C:14](=[CH:15][C:16]([CH:22]=[O:23])=[C:17]([O:20]C)[CH:18]=3)[CH2:13][CH2:12]2)[N:7]=[CH:6]1.O.[OH-].[NH4+]>C(Cl)Cl>[OH:20][C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][CH:11]2[CH2:10][C:8]2[N:7]=[CH:6][NH:5][CH:9]=2)=[CH:15][C:16]=1[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 178486438HCID 178486438, compound

Product 1

HCID 178519267HCID 178519267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide 1.0 M solution in methylene chloride (2 ml) is added dropwise to a stirred solution of 1-(1H-imidazol-4-ylmethyl)-6-methoxyindan-5-carbaldehyde (144 mg) in methylene chloride (10 ml) at −70° C. under a nitrogen atmosphere. After the addition the mixture is allowed to warm to room temperature and is stirred for 3 hours. The mixture is then poured into cold water and is made basic with ammonium hydroxide solution. The product is extracted into methylene chloride which is washed with water, dried with sodium sulfate and evaporated to dryness. The crude product is purified by flash chromatography using methylene chloride-methanol as eluent and crystallized from ethyl acetate.

Workup

  1. additionAfter the addition the mixture
  2. extractionThe product is extracted into methylene chloride which
  3. washis washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product is purified by flash chromatography
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-49ba6969e1824c9f88c6d74019791921
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Reaction notes

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