Potassium Carbonate → [4-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)-benzyl]-carbamic acid tert-butyl ester

HRID 1626718Notes

Reaction equation

[N:1]1([C:7]2[O:8][C:9]3[C:14]([C:15](=[O:17])[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3OS(C(F)(F)F)(=O)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:26]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:29]([O:28][C:26](=[O:27])[NH:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[O:8][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:16][C:15]3=[O:17])=[CH:39][CH:40]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

Trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl ester [E] (380 mg, 1.0 mmol), 4-(N-Boc-aminomethyl)phenylboronic acid (280 mg, 1.1 mmol, 1.1 eq), potassium carbonate (275 mg, 2.0 mmol, 2 eq) and tetrakis triphenylphosphine palladium (0) (60 mg, 0.05 mmol 0.05 eq) were stirred in dioxane (4 ml) and heated to 80° C. for 4 hours. The cooled reaction was then filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography eluting with 0-3% methanol in dichloromethane to afford [4-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)-benzyl]-carbamic acid tert-butyl ester [F]. Yield 238 mg, 54%.

Workup

customThe cooled reaction
filtrationwas then filtered
concentrationthe filtrate concentrated in vacuo
customThe residue was purified by flash chromatography
washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record: ord-43c16441137a409e91c9ebd9967789b9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

Loading…