Dichloromethane → HCID 86642897, compound

HRID 1036462Notes

Reaction equation

HRID 1036462 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([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)[CH:6]=[CH:5]2.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.C(Cl)Cl>C(N(CC)CC)C>[CH3:18][C:15]1([CH3:19])[O:16][CH2:17][C:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([C:29]([F:40])([F:39])[F:28])[CH:35]=4)[CH:3]=3)[CH:8]=2)[CH2:13][O:14]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 44228963Tert-butyl 5-(6-hydroxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86642897HCID 86642897, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

[5-(6-Hydroxy-naphthalen-2-yl)-2,2-dimethyl-1,3-dioxinan-5-yl]-carbamic acid tert-butyl ester (Example 13, 50.0 mg, 0.000134 mol), 3-(trifluoromethyl)phenylboronic acid (50.8 mg, 0.000268 mol), cupric acetate (24.3 mg, 0.000134 mol) were placed in a vial, purged with N2, following by methylene chloride (2 mL, 0.03 mol) and triethylamine to (0.0933 mL, 0.000669 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 (43 mg, 62%). 1H NMR (CHLOROFORM-d) δ: 7.84 (d, J=8.8 Hz, 1H), 7.79 (s, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.55 (dd, J=8.7, 1.6 Hz, 1H), 7.41-7.49 (m, 1H), 7.31-7.40 (m, 2H), 7.16-7.30 (m, 314), 5.57 (br. s., 1H), 4.22-4.29 (m, 2H), 4.14 (d, J=11.3 Hz, 2H), 1.49-1.58 (m, 6H), 1.36 (br. s., 9H). MS (M−113): 404.20.

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-b8bce0a7ac05431ea2ddb96528f5fa5c
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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