Potassium Carbonate → 5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amine

HRID 1882276Notes

Reaction equation

HRID 1882276 reaction equation
Br[C:2]1[CH:10]=[C:9]([NH2:11])[C:8]([O:12][CH3:13])=[C:7]2[C:3]=1[C:4]1[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:5]=1[NH:6]2.[CH2:19]([S:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH3:20].O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.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>[CH2:19]([S:21]([C:24]1[CH:29]=[C:28]([C:2]2[CH:10]=[C:9]([NH2:11])[C:8]([O:12][CH3:13])=[C:7]3[C:3]=2[C:4]2[CH:17]=[C:16]([CH3:18])[CH:15]=[N:14][C:5]=2[NH:6]3)[CH:27]=[CH:26][CH:25]=1)(=[O:22])=[O:23])[CH3:20]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 164271023-Ethylsulfonylphenylboronic acidHCID 588800855-bromo-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amine

Product 1

HCID 588800795-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amineYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL microwave vial was charged with Compound 238 (500 mg, 1.63 mmol), 3-(ethylsulfonyl)phenylboronic acid (419 mg, 1.96 mmol) and Pd(PPh3)4 (188 mg, 0.16 mmol). To the mixture was added dioxane (5 mL) and a saturated aqueous solution of K2CO3 (2.5 mL). The reaction mixture was heated at 140° C. for 20 min. in microwave. The reaction was diluted with EtOAc and washed with aqueous water and brine. The organic extracts were dried (Na2SO4) and concentrated and purified by flash chromatography to yield the title compound (528 mg, 82%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.33 Hz, 3H) 2.25 (s, 3H) 3.95 (s, 3H) 7.44 (br. s., 1H) 7.78 (br. s., 1H) 7.87 (d, J=7.58 Hz, 1H) 7.96 (d, J=3.28 Hz, 1H) 8.01 (d, J=7.33 Hz, 1H) 8.07 (br. s., 1H) 8.23 (br. s., 1H) 9.88 (br. s., 1H) 12.07 (br. s., 1H); [M+H] calc'd for C21H21N3O4S, 396.2; found, 396.3.

Workup

  1. washwashed with aqueous water and brine
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-03c7463376f04afdaa583f2d51e7e00d
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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