Ethyl Acetate → N-Cyclopropylmethyl-N-[7-(2,4-dimethoxy-6-methylphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-3-furanylmethylamine

HRID 1181879ノート

反応式

HRID 1181879 の反応式
Br[C:2]1[N:7]2[N:8]=[C:9]([CH2:22][CH3:23])[C:10]([N:11]([CH2:18][CH:19]3[CH2:21][CH2:20]3)[CH2:12][CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([CH3:34])[C:27]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(OCC)(=O)C>COCCOC.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>[CH:19]1([CH2:18][N:11]([C:10]2[C:9]([CH2:22][CH3:23])=[N:8][N:7]3[C:2]([C:27]4[C:28]([CH3:34])=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=4[O:25][CH3:24])=[CH:3][CH:4]=[CH:5][C:6]=23)[CH2:12][CH:13]2[CH2:17][CH2:16][O:15][CH2:14]2)[CH2:21][CH2:20]1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 17749109Barium hydroxide, octahydrateHCID 21984575N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-3-furanylmethylamineHCID 219847402,4-Dimethoxy-6-methylphenylboric acid

生成物 1

HCID 21984551N-Cyclopropylmethyl-N-[7-(2,4-dimethoxy-6-methylphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-3-furanylmethylamine収率 49.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

After dissolving N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-3-furanylmethylamine (150 mg) in 1,2-dimethoxyethane (20 mL) and water (10 mL), 2,4-dimethoxy-6-methylphenylboric acid (155 mg), tetrakis(triphenylphosphine)palladium (0) complex (92 mg) and barium hydroxide octahydrate (250 mg) were added and the mixture was heated and stirred at 80° C. for 1 hour. Water was added to the reaction mixture, extraction was performed with ethyl acetate, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the title compound (88 mg) was obtained from the n-hexane:ethyl acetate (6:1) fraction as a yellow oil.

後処理

  1. additionwere added
  2. temperaturethe mixture was heated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-608ed721c2b14835add4aab0a547758c
出典データセット
uspto-grants-2007_10
特許番号
US07285666B2

反応ノート

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