Ethyl bromopyruvate → HCID 57703746, compound

HRID 1632034Notes

Reaction equation

HRID 1632034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=3)[C:9]=2[F:24])[CH:5]=[CH:6][CH:7]=1.Br[CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29].C([O-])(O)=O.[Na+]>COCCOC>[CH2:31]([O:30][C:28]([C:27]1[N:23]=[C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C:10]3[C:9]([F:24])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[C:13]([O:14][CH3:15])=[CH:12][CH:11]=3)=[CH:22][N:21]2[CH:26]=1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 57703709HCID 57703709, compound

Product 1

HCID 57703746HCID 57703746, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Into a 20 mL vial with stir bar was added 5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-ylamine (P-252, 565 mg, 1.65 mmol), ethyl bromopyruvate (0.52 mL, 4.12 mmol), and 5 mL of DME. The reaction was stirred at room temperature for 18 hours, then basified with NaHCO3 (aq. sat). The product was extracted with ethyl acetate and concentrated. Purification by flash column chromatography (5% acetone/dichloromethane) provided a tan solid which was triturated with ether to obtain 6-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (I-37) (198 mg, 27%) as an off-white solid.

Workup

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. extractionThe product was extracted with ethyl acetate
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (5% acetone/dichloromethane)
  5. customprovided a tan solid which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-2968deec55db4d1681ccd24e5f8dfb13
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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