Potassium Carbonate → {1-[4-(8-ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037401Notes

Reaction equation

HRID 1037401 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([C:29]#[C:30][Si](C)(C)C)[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([C:29]#[CH:30])[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67067912(1-[4-(4-oxo-2-phenyl-8-trimethylsilanylethynyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 86671055{1-[4-(8-ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of {1-[4-(4-oxo-2-phenyl-8-trimethylsilanylethynyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (51 mg, 0.091 mmol) in MeOH (2 mL) and DCM (1 mL) was treated with potassium carbonate (15 mg, 0.109 mmol) and the reaction stirred at RT for 3 h. The reaction mixture was quenched with water, diluted with EtOAc, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a foamy solid (45 mg, 100%). 1H NMR (400 MHz, CDCl3): δ 8.27 (dd, J=7.7 and 1.6 Hz, 1H), 7.86 (dd, J=7.5 and 1.6 Hz, 1H), 7.48 (d, J=7.5 Hz, 2H), 7.41-7.30 (m, 5H), 7.25-7.19 (m, 3H), 5.06 (s, 1H), 3.47 (s, 1H), 2.65-2.27 (m, 4H), 2.14-2.00 (m, 1H), 1.91-1.76 (m, 1H), 1.37 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f09974c9cdf40fdbab82aeb9e8040ab
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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