Tetrahydrofuran → HCID 21865601, compound

HRID 857276Notes

Reaction equation

HRID 857276 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=O)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:14]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH2:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 21865558HCID 21865558, compound

Product 1

HCID 21865601HCID 21865601, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl-triphenyl phosphonium bromide (1.15 eq) in THF (0.3M) at 0° C. was added K-tOBu (1.15 eq). The resulting mixture was stirred for 30 min after which a solution of the 8-bromo-quinoline-6-carbaldehyde from Step 1 (1.0 eq) was added. The final mixture was stirred at room temperature for 12 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1) afforded the desired compound as a yellow solid.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f423bf26d5614cd78d1b9cf6b854c7dd
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

Loading…