Water → HCID 178519269, compound

HRID 428633Notes

Reaction equation

HRID 428633 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]([O:22]C)=[C:17]([CH:20]=[O:21])[CH:18]=3)[CH2:13][CH2:12]2)[N:7]=[CH:6]1.O.[OH-].[NH4+]>C(Cl)Cl>[OH:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:11]([CH2:10][C:8]3[N:7]=[CH:6][NH:5][CH:9]=3)[CH2:12][CH2:13]2)=[CH:18][C:17]=1[CH:20]=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 178486436HCID 178486436, compound

Product 1

HCID 178519269HCID 178519269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide 1.0 M solution in methylene chloride (3.9 ml) is added dropwise to a stirred solution of 3-(1H-imidazol-4-ylmethyl)-6-methoxyindan-5-carbaldehyde (318 mg) in methylene chloride (15 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. Work-up of the mixture gives the crude product which is purified by flash chromatography and recrystallized from ethyl acetate.

Workup

  1. additionAfter the addition the mixture

Sources & evidence

ORD record
ord-d204fcbaa12e4b0b900d59805fca7494
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Reaction notes

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