Ethyl bromoacetate → HCID 54678064, compound

HRID 1244098Notes

Reaction equation

HRID 1244098 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37]CC)=[O:36]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]([C:7]1[C:6](=[O:10])[NH:5][C:4]2[S:11][CH:12]=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH2:34][C:35]([OH:37])=[O:36])=[CH:18][CH:19]=3)[C:3]=2[C:2]=1[OH:1])#[N:9]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54708532A-769662

Product 1

HCID 54678064HCID 54678064, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.090 g, 0.25 mmol) in acetone (20 mL) was added potassium carbonate (0.140 g, 1 mmol) and tetrabutylammonium iodide (0.004 g, 0.0125 mmol) and stirred for 30 min at room temperature. Ethyl bromoacetate (0.083 g, 0.5 mmol) was then added to the reaction mixture and stirred for an additional 16 h at room temperature. The reaction mixture was concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 416.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.44 (br s, 1H), 7.57 (d, 2H), 7.46 (d, 2H), 7.30–7.36 (m, 2H), 7.07 (d, 1H), 7.04 (s, 1H), 6.99 (d, 1H), 4.74 (s, 2H).

Workup

  1. stirringstirred for an additional 16 h at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-724ce01303964b6fb032aaaa69f5d262
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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