Water → HCID 67130904, compound

HRID 1259838Notes

Reaction equation

HRID 1259838 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[N:14]=2)[N:9]=[CH:8][C:7]=1[F:18])[CH3:2].Br[CH2:21][C:22]#[N:23].O>C1COCC1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[N:14]=2)[N:9]=[CH:8][C:7]=1[F:18])[CH2:21][C:22]#[N:23])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11534BromoacetonitrileHCID 67134602Ethyl (3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)acetate

Product 1

HCID 67130904HCID 67130904, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

LiRMDS in THF (1M; 12.5 mL) was added at −78° C. during 15 min to a solution of (3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-acetic acid ethyl ester (3.00 g; prepared in analogy to the corresponding methyl ester described in WO 2007/122258) in THF (30 mL). The resulting orange mixture was stirred at −78° C. for 2 h. Bromoacetonitrile (1.13 mL) was added dropwise and the reaction mixture was further stirred at −78° C. for 2 h. The reaction mixture was treated with water and extracted with EA. The combined org. phases were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by CC (Hept/EA 2:1 to 1:1) affording a yellow oil (3.09 g; 89.7% yield).

Workup

  1. stirringthe reaction mixture was further stirred at −78° C. for 2 h
  2. extractionextracted with EA
  3. washphases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by CC (Hept/EA 2:1 to 1:1)
  8. customaffording a yellow oil (3.09 g; 89.7% yield)

Sources & evidence

ORD record
ord-97ec2514350847c0a93d81b1a6ce8d73
Source dataset
uspto-grants-2013_06
Patent number
US08466168B2

Reaction notes

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