Sodium Hydroxide → HCID 86721349, compound

HRID 869521Notes

Reaction equation

HRID 869521 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]([O:30]C)[C:24]=4[N:23]=[C:22]3[CH2:32][O:33]C)[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]([OH:30])[C:24]=4[N:23]=[C:22]3[CH2:32][OH:33])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 86721348HCID 86721348, compound

Product 1

HCID 86721349HCID 86721349, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[step 4] (E)-2-(3-fluoro-8-{[4-methoxy-2-(methoxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (1.0 g, 2.1 mmol) obtained in step 3 was dissolved in dichloromethane (11 mL), boron tribromide (21.0 mL, 21.0 mmol, 1.0 mol/L dichloromethane solution) was added at 0° C., and the mixture was stirred at room temperature for 2 hr. To the mixture was added 2 mol/L aqueous sodium hydroxide solution, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v) to give (E)-2-(3-fluoro-8-{[4-hydroxy-2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (0.7 g, 75%).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v)

Sources & evidence

ORD record
ord-be224fc9275740f1b8e24bbbe057f412
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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