Ammonium Hydroxide → HCID 68788744, compound

HRID 1801472Notes

Reaction equation

HRID 1801472 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.[CH2:21]([Sn](CCCC)(CCCC)CCCC)[CH:22]=[CH2:23].[Li+].[Cl-].[NH4+].[OH-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC.CN(C=O)C>[CH2:23]([C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2)[CH:22]=[CH2:21]

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Product 1

HCID 68788744HCID 68788744, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A flask charged with trifluoro-methanesulfonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (2.50 g, 8.11 mmol; prepared according to WO 2007/107965), allyltributyltin (3.11 mL, 1.25 eq.) and DMF (20 mL) was degassed with 1\12. LiCl (1.29 g, 3.75 eq.) and Pd(PPh3)4 (234 mg, 0.025 eq.) were added and the mixture was stirred at 100° C. for 2 h. After cooling to rt the mixture was poured into 10% aq. NH4OH and EA, the aq layer was extracted with EA and the combined org. layers were washed with water (2×) and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 2:1) to afford the title intermediate as a yellow oil (1.59 g, 98% yield).

Workup

  1. customwas degassed with 1\12
  2. temperatureAfter cooling to rt the mixture
  3. extractionthe aq layer was extracted with EA
  4. washlayers were washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by CC (Hept/EA 2:1)

Sources & evidence

ORD record
ord-adc24632f5a146e9a5c24796a0ea7d24
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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