Potassium Phosphate, Tribasic → HCID 10164661、化合物

HRID 2213842

反応式

HRID 2213842 の反応式
[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[N:18]=[CH:17][C:16]([C:21]#[N:22])=[C:15]3Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:28][C:29]1[CH:35]=[C:34]([F:36])[C:33]([O:37][CH3:38])=[CH:32][C:30]=1[NH2:31].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[N:18]=[CH:17][C:16]([C:21]#[N:22])=[C:15]3[NH:31][C:30]1[CH:32]=[C:33]([O:37][CH3:38])[C:34]([F:36])=[CH:35][C:29]=1[Cl:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 21956464HCID 21956464、化合物HCID 219564782-Chloro-4-fluoro-5-methoxybenzenamine

生成物 1

HCID 10164661HCID 10164661、化合物収率 36%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 8-(benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile (1.00 g, 2.7 mmol), 2-chloro-4-fluoro-5-methoxyaniline (560 mg, 3.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (240 mg, 0.26 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (330 mg, 0.84 mmol) and K3PO4 (860 mg, 4.1 mmol) in 15 mL of ethylene glycol dimethyl ether is heated at 80° C. for 3 hours. An additional 5% of all reagents is added and the mixture is heated at 80° C. for 2 hours then cooled to room temperature and partitioned between aqueous sodium bicarbonate and methylene chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography eluting with 1:1 hexane/ethyl acetate yields 500 mg (36%) of 8-(benzyloxy)-4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp 248–250° C. dec.

後処理

  1. temperaturethe mixture is heated at 80° C. for 2 hours
  2. temperaturethen cooled to room temperature
  3. custompartitioned between aqueous sodium bicarbonate and methylene chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography
  8. washeluting with 1:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-5761a33390cf4c2383139b40e1bb498a
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

関連ノート

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