Potassium Carbonate → HCID 56832512, compound

HRID 656573Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:8](=[O:13])[CH2:7][CH:6]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3Br)[CH2:5][C:4]=2[N:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[N:25]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC(N(C)C)=O>[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:8](=[O:13])[CH2:7][CH:6]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[N:25]=3)[CH2:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a 5 mL microwave vial was added 2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydroquinazolin-5(6H)-one (1F (Example 1), 56 mg, 0.163 mmol, 1.0 eq.), 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (77 mg, 0.325 mmol, 2.0 eq.), Pd(dppf)Cl2 (11 mg, 0.013 mmol, 0.08 eq.), 2.0 M aqueous K2CO3 (162 μL, 0.325 mmol, 2.0 eq.), and dimethylacetamide (2 mL). The vial was sealed and heated in a microwave at 150° C. for 10 min. LC/MS analysis showed the reaction was completed. The reaction mixture was filtered through Celite and purified via preparative-HPLC to give the product 13A as a white solid (33 mg, 55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.54 (s, 3H) 2.62 (ddd, J=15.73, 3.03, 2.72 Hz, 1H) 2.84-3.04 (m, 2H) 3.15-3.31 (m, 1H) 3.60-3.73 (m, 1H) 3.78 (s, 3H) 6.81 (d, J=8.34 Hz, 1H) 7.15 (d, J=7.07 Hz, 1H) 7.22 (dd, J=9.60, 2.78 Hz, 1H) 7.33 (td, J=8.59, 2.78 Hz, 1H) 7.55 (br. s., 2H) 7.71 (dd, J=8.84, 5.81 Hz, 1H) 7.81 (dd, J=8.34, 7.33 Hz, 1H). ESI-MS: m/z 379.3 (M+H)+.

Workup

customThe vial was sealed
filtrationThe reaction mixture was filtered through Celite
custompurified via preparative-HPLC

Sources & evidence

ORD record: ord-7a9ba0012f0948749206a61e714805de
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071766B2

Reaction notes

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