4-Hydroxymethylpyridine → HCID 58923379, compound

HRID 1951051Notes

Reaction equation

HRID 1951051 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[C:11]1[C:10]([OH:17])=[CH:9][C:8]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:7][C:6]=1[O:5]2.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CS(C)=O>[OH:17][C:10]1[C:11]2[C:12](=[O:16])[C:13]3[C:4](=[CH:3][C:2]([O:31][CH2:30][C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)=[CH:15][CH:14]=3)[O:5][C:6]=2[CH:7]=[C:8]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:9]=1

Participants

5

Reactant 3

HCID 114724-HydroxymethylpyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11209251HCID 11209251, compound

Product 1

HCID 58923379HCID 58923379, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

6-Fluoro-1-hydroxy-3-morpholin-4-yl-xanthen-9-one (16 mg, 0.05 mmol) and 4-pyridylmethanol (8 mg, 0.07 mmol) were dissolved in DMSO (0.25 mL) and KHMDS (0.5 M in toluene, 0.24 mL) was added. The reaction mixture was heated at 80° C. for 16 hours. The reaction mixture wad quenched with sat. NH4Cl/water (1:1, 2 mL) and the solids were filtered. The solid was purified via flash chromatography eluting with CH2Cl2/MeOH (98:2) to produce 3.9 mg (20%). 1H NMR (CDCl3, 400 MHz) δ: 12.80 (s, 1H), 8.66 (s, 2H), 8.16 (d, 1H), 7.38 (d, 2H), 7.00 (d, 1H), 6.80 (s, 1H), 6.27 (dd, 1H), 6.25 (s, 1H), 5.21 (s, 2H), 3.86-3.83 (m, 4H), 3.37-3.35 (m, 4H). LRMS (APCI, positive): Da/e 405.1 (m+1).

Workup

  1. customThe reaction mixture wad quenched with sat. NH4Cl/water (1:1, 2 mL)
  2. filtrationthe solids were filtered
  3. customThe solid was purified via flash chromatography
  4. washeluting with CH2Cl2/MeOH (98:2)
  5. customto produce 3.9 mg (20%)

Sources & evidence

ORD record
ord-85aaf5fa5c984259a1f7b5f318fe9d63
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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