Bromine → HCID 11691204, compound

HRID 1176673Notes

Reaction equation

HRID 1176673 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)[C:7]1=[NH:24].[Br:29]Br.C([O-])(O)=O.[Na+]>ClCCl>[F:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[F:22])[CH2:15][N:8]1[C:9]2[CH:14]=[CH:13][C:12]([Br:29])=[CH:11][C:10]=2[N:6]([CH2:5][C:4]2[CH:25]=[CH:26][C:27]([F:28])=[C:2]([F:1])[CH:3]=2)[C:7]1=[NH:24]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 11689553HCID 11689553, compound

Product 1

HCID 11691204HCID 11691204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Bis(3,4-difluorobenzyl)-1,3-dihydrobenzoimidazol-2-ylideneamine, prepared by Procedure A, was dissolved in dichloromethane, added bromine (2 eq) and stirred overnight at rt. Saturated aqueous NaHCO3 was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, concentrated in vacuo and purified by preparative LCMS to give the title compound as the free base (solid, mp 88-89.5° C.). MS(ES+) m/z 465 ([M+1]+, 100). 1NMR (DMSO-d6) δ 5.05 (s, 4H), 6.08 (br s, 1H), 6.85-6.93 (m, 1H), 6.98-7.23 (m, 4H), 7.35-7.45 (m, 4H).

Workup

  1. extractionthe mixture extracted with EtOAc
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-1a21e9c6efaa403a87b1a39977cfb8de
Source dataset
uspto-grants-2010_11
Patent number
US07842817B2

Reaction notes

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