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CAS No. : | 882672-05-1 | MDL No. : | MFCD09261000 |
Formula : | C8H4BrClN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NYQBZJFZEZEXFP-UHFFFAOYSA-N |
M.W : | 243.49 | Pubchem ID : | 17913559 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
510 mg | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; at 90℃; for 1h;Inert atmosphere; | (i) Methyl 3-(2-chloroguinazolin-6-yl)-4-methylbenzoateA mixture of 6-bromo-2-chloroquinazoline (780 mg, 3.20 mmol) and methyl 4-methyl-3- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate (1000 mg, 3.62 mmol) in 1,2- dimethoxyethane (3 mL) and 1 M NaHCO3 solution (10 mL, 10.00 mmol) was purged with nitrogen for 5 minutes. The mixture was heated to 90C before adding Pd(Ph3P)4 (200 mg, 0.173 mmol) and stirring for 1 h. The mixture was diluted with water (150 mL) and extracted with diethyl ether (3 x 150 mL). The combined organic phases were washed with water (150 mL), 20 % brine (150 mL) and saturated brine (150 mL). The organic phase was dried (MgSO4) and concentrated to give a yellow oil which was purified by chromatography on the Companion (80 g column, 0-30% EtOAc/isohexane) to afford the sub-title compound (510 mg) as a cream solid.LCMS mlz 313 (M+H) (ES) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In isopropyl alcohol; at 100℃; for 2h;Inert atmosphere; | To a mixture of 6-bromo-2-chloroquinazoline (18) (100 mg, 0.41 mmol) and (15c) (85 mg, 0.49 mmol), propan-2-ol (2 mL) was added and the reaction mixture was heated at 100 C for 2 h. After completion, the reaction mixture was cooled to rt, concentrated and purified by column chromatography using silica gel (2% MeOH/DCM) to afford 19c (150 mg, 97%) as light yellow solid. lH NMR (600 MHz, DMSO-d<5) delta (ppm) 10.46 (s, 1H), 9.37 (s, 1H), 8.71 (s, 1H), 8.25-8.22 (m, 2H), 7.97 (d, / = 8.1 Hz, 1H), 7.65- 7.60 (m, 2H), 7.55-7.54 (m, 1H), 3.23 (s, 3H). |
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