Dichloromethane → HCID 67412838, compound

HRID 2389118Notes

Reaction equation

HRID 2389118 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(Cl)Cl.C(N(CC)CC)C>>[CH3:18][C@@:12]1([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([C:20]([F:31])([F:30])[F:19])[CH:26]=4)[CH:3]=3)[CH:8]=2)[CH2:16][O:15][C:14](=[O:17])[NH:13]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67412838HCID 67412838, compoundYield 31%

Procedure

(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (Example 4, 65 mg, 0.27 mmol), 3-(trifluoromethyl)phenylboronic acid (101 mg, 0.54 mmol) and cupric acetate (48.5 mg, 0.000267 mol) were placed in a vial, purged with N2, following by methylene chloride (2 mL, 0.03 mol) and triethylamine (0.186 mL, 0.00134 mol) at 23° C. The reaction was allowed to stir for about for 10 hours, and filtrated. The crude material was then purified via chromatography (SiO2, 4 g, 0-35%) to give a pure product (22 mg, 31%). 1H NMR (CHLOROFORM-d) δ: 7.87 (d, J=9.0 Hz, 1H), 7.83 (s, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.45-7.52 (m, 2H), 7.37-7.43 (m, 1H), 7.35 (d, J=2.0 Hz, 1H), 7.27-7.31 (m, 2H), 7.22 (d, J=8.3 Hz, 1H), 6.01 (s, 1H), 4.39-4.49 (m, 2H), 1.87 (s, 3H). MS (M+1): 388.20.

Workup

  1. custompurged with N2
  2. filtrationfiltrated
  3. customThe crude material was then purified via chromatography (SiO2, 4 g, 0-35%)

Sources & evidence

ORD record
ord-f827126c3dd14a1b8f0e1d15b1afd06d
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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