Potassium Carbonate → 1-(2,3-Dihydropyrano[4,3,2-de]quinolin-7-yl)-3-methylnaphthalen-2-ol

HRID 514005Notes

Reaction equation

HRID 514005 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13].OC(C(F)(F)F)=O.[O:21]1[C:32]2[C:33]3[C:28]([C:29](B(O)O)=[CH:30][CH:31]=2)=[N:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:21]1[C:32]2[C:33]3[C:28]([C:29]([C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[CH:5]=[C:4]([CH3:12])[C:3]=4[OH:13])=[CH:30][CH:31]=2)=[N:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 671260591-Bromo-3-methylnaphthalen-2-olHCID 1317332892,3-dihydropyrano[4,3,2-de]quinolin-7-ylboronic acid TFA salt

Product 1

HCID 671260371-(2,3-Dihydropyrano[4,3,2-de]quinolin-7-yl)-3-methylnaphthalen-2-olYield 29.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

1-Bromo-3-methylnaphthalen-2-ol (5B) (340 mg, 1.43 mmol), 2,3-dihydropyrano[4,3,2-de]quinolin-7-ylboronic acid TFA salt (5C) (566 mg, 1.72 mmol), Pd(PPh3)4 (166 mg, 0.14 mmol) and K2CO3 (991 mg, 7.15 mmol) were added to a degassed solution of DMA (6 mL) and water (2 mL) and heated to 110° C. in a microwave for 1 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give 5D (136 mg, 29%). LCMS-ESf+ (m/z): [M+H]+ calcd for C22H18NO2: 328.38. Found: 328.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c8aee430d6b14871b4531e891e8a4ad9
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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