Sodium Carbonate → HCID 11462486、化合物

HRID 1247449ノート

反応式

HRID 1247449 の反応式
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

参加物

10

反応物 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、化合物

生成物 1

HCID 11462486HCID 11462486、化合物収率 14.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-3974da0a13f040d4b4cb6919e4a07e55
出典データセット
uspto-grants-2006_10
特許番号
US07129260B2

反応ノート

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