HCID 12838740, compound → HCID 68709642, compound

HRID 1513536Notes

Reaction equation

HRID 1513536 reaction equation
[OH:1][C:2]1[C:11]2[CH:12]=[CH:13][O:14][C:10]=2[C:9]([OH:15])=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6](C)[O:7]2.Br[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][CH2:19][O:15][C:9]2[C:10]3[O:14][CH:13]=[CH:12][C:11]=3[C:2]([OH:1])=[C:3]3[C:8]=2[O:7][CH:6]=[CH:5][C:4]3=[O:17])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 12838740HCID 12838740, compoundHCID 147371331-(3-Bromopropyl)-4-fluorobenzene

Product 1

HCID 68709642HCID 68709642, compoundYield 66%

Procedure

4,9-Dihydroxy-7-methyl-5H-furo[3,2-g]chromen-5-one (2.32 g, 10 mmol) was reacted with 1-bromo-3-(4-fluorophenyl)propane (1.0 eq) according to General Procedure A to give 9-(3-[4-fluorophenyl]propoxy)-4-hydroxy-5H-furo[3,2-g]chromen-5-one (2.4 g, 66%), that was further reacted according to General Procedure D (Step 1) to provide the corresponding triflate derivative in 80% (2.6 g) yield. The triflate (2.5 g, 5.0 mmol), ZnBr2.2H2O (3.92 g, 15.0 mmol), CuI (47.5 mg, 0.25 mmol), PdCl2(PPh3)2 (105 mg, 0.15 mmol) and MeLi (9.4 mL of 1.6 M in diethylether, 15.0 mmol) were reacted according to General Procedure D (Step 2) and the crude material was purified by silica-gel flash chromatography, eluting with dichloromethane to afford the title compound as a off-white solid (1.2 g, 65%). 1H NMR (300 MHz, CDCl3): δ 2.06-2.15 (m, 2H), 2.36 (s, 3H, Me), 2.89 (t, J=7.6 Hz, 2H, CH2), 2.96 (s, 3H), 4.37 (t, J=6.3 Hz, CH2), 6.05 (s, 1H), 6.92-6.99 (m, 3H), 7.15-7.20 (m, 2H), 7.64 (d, J=2.1 Hz, 1H).

Sources & evidence

ORD record
ord-b4b89fa96ef64e548102aaafcd4f6acd
Source dataset
uspto-grants-2012_07
Patent number
US08217189B2

Reaction notes

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