Sodium Carbonate → HCID 11462486, compound

HRID 1247449Notes

Reaction equation

HRID 1247449 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][NH:12][C:13]3=[O:18])O1.Br[C:21]1[N:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)=[O:29])=[CH:23][CH:22]=1.NC1C=C(Br)C=CN=1.C1(C)C=CC=C(N=C=O)C=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)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>[CH3:37][C:33]1[CH:32]=[C:31]([NH:30][C:28]([NH:27][C:24]2[CH:25]=[N:26][C:21]([C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH2:11][NH:12][C:13]4=[O:18])=[CH:22][CH:23]=2)=[O:29])[CH:36]=[CH:35][CH:34]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 69303m-Tolyl isocyanateHCID 6932822-Amino-4-bromopyridineHCID 219075244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-oneHCID 21907539HCID 21907539, compound

Product 1

HCID 11462486HCID 11462486, compoundYield 14.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of Example 54A (259 mg, 1 mmol) and N-(6-bromo-3-pyridinyl)-N′-(3-methylphenyl)urea (367 mg, 1.2 mmol) (prepared from 2-amino-4-bromopyridine and m-tolylisocyanate following the procedure of Example 1E) in toluene (6 mL) and ethanol (6 mL) was degassed with N2 then treated sequentially with a solution of Na2CO3 (509 mg, 4.8 mmol) in water (3 mL) and tetrakis(triphenylphosphine)palladium (0) (208 mg, 0.187 mmol) and stirred at reflux overnight. The resulting suspension was cooled to room temperature, diluted with diethyl ether, and filtered. The filter cake was washed with water, diethyl ether, dichloromethane, ethyl acetate, and methanol. The combined filtrates were concentrated to give 51 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 10.35 (s,1H), 9.58 (s,1H), 8.73 (s, 1H), 8.56 (s,1H), 8.06 (d, J=6 Hz, 1H), 7.56–7.81 (m, 4H), 7.3–7.46 (m, 2H), 7.20 (t, J=6 Hz, 1H), 6.85 (d, J=6 Hz, 1H), 4.56 (s, 2H), 2.31 (s,3H); MS (ESI(+)) m/e 359 (M+H)+.

Workup

  1. customethanol (6 mL) was degassed with N2
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. washThe filter cake was washed with water, diethyl ether, dichloromethane, ethyl acetate, and methanol
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-3974da0a13f040d4b4cb6919e4a07e55
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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