3-Pyridinemethanol → HCID 58923375, compound

HRID 1951050Notes

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][CH:27]=[C:26]([CH2:30][OH:31])[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:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=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

Conditions

Temperature: 80 °C

Procedure

6-Fluoro-1-hydroxy-3-morpholin-4-yl-xanthen-9-one (16 mg. 0.05 mmol) and 3-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 to 80° C. for 16 hours, then stirred at room temperature for 60 hours. The reaction was quenched with sat. NH4Cl/water (1:1, 2 mL) and the solids were filtered. The crude solid was purified via flash chromatography eluting with CH2Cl2/MeOH (98:2) to yield 6.8 mg (34%) of product. 1H NMR (CDCl3, 400 MHz) δ: 12.80 (s, 1H), 8.73 (s, 1H), 8.64 (d, 1H), 8.15 (d, 1H), 7.80 (d, 1H), 7.36 (dd, 1H), 6.97 (dd, 1H) 6.85 (s, 1H), 6.27 (s, 1H), 6.24 (s, 1H), 5.19 (s, 2H), 3.86-3.83 (m, 4H), 3.37-3.35 (m, 4H). LRMS (APCI, positive): Da/e 405.1 (m+1).

Workup

customThe reaction was quenched with sat. NH4Cl/water (1:1, 2 mL)
filtrationthe solids were filtered
customThe crude solid was purified via flash chromatography
washeluting with CH2Cl2/MeOH (98:2)

Sources & evidence

ORD record: ord-70b434c2f665433b92b46e0afa45d2c3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404681B2

Reaction notes

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