Ethyl Acetate → HCID 67336886, compound

HRID 1673199Notes

Reaction equation

HRID 1673199 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]2[CH:13]=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:25][C:26](=[O:30])[O:27][CH2:28][CH3:29]>O>[O:27]1[C:26]2([CH2:10][CH2:5][CH:6](/[CH:13]=[CH:13]/[C:6]3[CH:7]=[CH:8][N:9]=[C:10]4[C:5]=3[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]4)[CH2:7][CH2:25]2)[O:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 665231381,5-Naphthyridine-4-carboxaldehyde, 6-methoxy-

Product 1

HCID 67336886HCID 67336886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-60 °C

Procedure

A suspension of 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (2.0 g, 10.6 mmol, prepared according to WO 2006/032466) and intermediate 16.ii (4.5 g, 12.3 mmol) in 1,2-DME (60 ml) was cooled to −60° C. KHMDS (0.5M in THF, 42 ml, 20.9 mmol) was added dropwise over 1 h. The resulting black solution was allowed to reach rt over 2 h. It was diluted with water (40 ml) and EA (200 ml). The yield after work up and chromatography (Hex/EA 1:1) was 2.47 g (71%; yellow oil).

Workup

  1. customThe yield after work up

Sources & evidence

ORD record
ord-f516dc2e5fa14dbb8cd6e8bd0cad57c8
Source dataset
uspto-grants-2011_08
Patent number
US07999115B2

Reaction notes

Loading…