Water → (2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

HRID 1170073ノート

反応式

HRID 1170073 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=1

参加物

8

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

生成物 1

HCID 68433822(2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 8 mL 1,2-dimethoxyethane and 4 mL 1M sodium carbonate solution. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Phenylboronic acid (88 mg, 0.699 mmol), palladium(II)acetate (7 mg, 0.029 mmol) and triphenylphosphine (16 mg, 0.058 mmol) were added. The reaction mixture was refluxed overnight. The reaction mixture was poured into 100 mL water and extracted three times with ethyl acetate (100 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a white solid (191 mg, 96%), MS: m/e=341.3 (M+H+).

後処理

  1. customThe reaction mixture was evacuated
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. extractionextracted three times with ethyl acetate (100 mL each)
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

出典と根拠

ORDレコード
ord-21d65a832b624175ad5713536a122c5a
出典データセット
uspto-grants-2010_11
特許番号
US07825253B2

反応ノート

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