Water → HCID 66611737, compound

HRID 1467382Notes

Reaction equation

HRID 1467382 reaction equation
B(Br)(Br)Br.ClCCl.C([O:15][C:16]1[C:25]([O:26][CH3:27])=[CH:24][C:23]2[N:22]=[CH:21][C:20]3[N:28]([CH3:41])[C:29](=[O:40])[N:30]([C:31]4[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][C:32]=4[F:39])[C:19]=3[C:18]=2[CH:17]=1)C1C=CC=CC=1.O>FC(F)(F)C(O)=O>[F:39][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:31]=1[N:30]1[C:19]2[C:18]3[CH:17]=[C:16]([OH:15])[C:25]([O:26][CH3:27])=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:28]([CH3:41])[C:29]1=[O:40])[C:35]#[N:36]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 56847277HCID 56847277, compound

Product 1

HCID 66611737HCID 66611737, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A boron tribromide solution in dichloromethane (1.0 M, 14.5 ml, 14.5 mmol) was slowly added dropwise with ice-bath cooling in a dry nitrogen atmosphere to a solution of 4-(8-benzyloxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)-3-fluorobenzonitrile (1.45 g, 3.19 mmol) in trifluoroacetic acid (29 ml). When the addition was complete, the mixture were subsequently stirred for a further 30 min. When the reaction was complete (HPLC-MS check), the reaction mixture was carefully added to water (700 ml) and extracted twice with ethyl acetate (290 ml each time). The combined organic phases were washed with water (100 ml) and semi-saturated NaHCO3 solution (150 ml), subsequently dried using Na2SO4 and filtered with suction. The filtrate was evaporated in vacuo, and the residue was chromatographed over flash silica gel (solvent gradient ethyl acetate/0-33% by vol. of ethanol), giving 3-fluoro-4-(8-hydroxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile (1.10 g, 3.03 mmol), as solid. MS: 365.1 (M+H+), TLC (HPTLC): Rf=0.46 (ethyl acetate/ethanol 2:1, parts by volume).

Workup

  1. additionWhen the addition
  2. extractionextracted twice with ethyl acetate (290 ml each time)
  3. washThe combined organic phases were washed with water (100 ml) and semi-saturated NaHCO3 solution (150 ml)
  4. customsubsequently dried
  5. filtrationfiltered with suction
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was chromatographed over flash silica gel (solvent gradient ethyl acetate/0-33% by vol. of ethanol)

Sources & evidence

ORD record
ord-5664af1081834d979a6c4cd3be0ab5c0
Source dataset
uspto-grants-2015_04
Patent number
US09000153B2

Reaction notes

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