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Potassium Phosphate, Tribasic → 6-benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine

HRID 1890755
ノート
印刷プレビュー

反応式

HRID 1890755 の反応式
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[N:13][C:14]=2Br)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([C:29]2[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=2[CH3:36])[NH2:32])[N:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:32][C:31]3[CH:33]=[CH:34][C:35]([CH3:36])=[C:29]([C:21]4[N:20]=[CH:19][C:28]5[C:23]([CH:22]=4)=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:30]=3)=[N:13][CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223354025-Bromo-1,2,3,4-tetrahydro-2-(phenylmethyl)-2,6-naphthyridineHCID 583178853-(Isoquinolin-3-yl)-4-methylaniline

生成物 1

HCID 583180566-benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To the reaction vessel containing 2-benzyl-5-bromo-1,2,3,4-tetrahydro-2,6-naphthyridine (272 mg, 0.9 mmol), 3-(isoquinolin-3-yl)-4-methylaniline (210 mg, 0.9 mmol), Pd2(dba)3 (41 mg, 0.045 mmol), Xantphos (52 mg, 0.09 mmol) and K3PO4 (477 mg, 2.25 mmol) is added anhydrous dioxane (5 mL). The vessel is flushed with nitrogen, sealed and heated to 100° C. for 18 hours. The reaction is then cooled to ambient temperature, filtered through a celite pad to remove any salts. The filtrate is concentrated and purified by silica gel flash chromatography to afford 6-benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine as an off-white solid. MS m/z 457.2 (M+1).

後処理

  1. customThe vessel is flushed with nitrogen
  2. customsealed
  3. temperatureThe reaction is then cooled to ambient temperature
  4. filtrationfiltered through a celite pad
  5. customto remove any salts
  6. concentrationThe filtrate is concentrated
  7. custompurified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-91a71171fb6c4e11afaef8f73e00f7d0
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507491B2

反応ノート

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