Hydrochloric Acid → HCID 178429298, compound

HRID 2235439Notes

Reaction equation

HRID 2235439 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33]C)[CH2:5][N:6]1[C:14]2[CH:13]=[C:12]3[NH:15][C:16]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:17][C:11]3=[CH:10][C:9]=2[C:8]([CH3:28])([CH3:27])[C:7]1=[O:29].B(Br)(Br)Br.Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[OH:33])[CH2:5][N:6]1[C:14]2[CH:13]=[C:12]3[NH:15][C:16]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:17][C:11]3=[CH:10][C:9]=2[C:8]([CH3:28])([CH3:27])[C:7]1=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 178490846HCID 178490846, compound

Product 1

HCID 178429298HCID 178429298, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[5-(3-Fluoro-4-methoxy-benzyl)-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (105 mg) is suspended in a BBr3 solution in CH2Cl2 (1 M; 700 μl) and stirred at RT for 18 h. After addition of hydrochloric acid (400 μl; 1 N) the mixture is stirred at RT for another 1 h and then evaporated to dryness. The crude material is purified by preparative RP-HPLC, eluted with MeCN/water to yield the desired compound (25 mg).

Workup

  1. stirringis stirred at RT for another 1 h
  2. customevaporated to dryness
  3. customThe crude material is purified by preparative RP-HPLC
  4. washeluted with MeCN/water

Sources & evidence

ORD record
ord-c551d1cbbeb244d5850a39c7b192f02d
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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