Sodium Carbonate → HCID 11462486, 화합물

HRID 1247449노트

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HRID 1247449 반응식
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

참가 물질

10

반응물 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, 화합물

생성물 1

HCID 11462486HCID 11462486, 화합물수율 14.2%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3974da0a13f040d4b4cb6919e4a07e55
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129260B2

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