Cesium carbonate → 2-(Isoquinolin-3-ylamino)-4-(4-tert-butoxycarbonylpiperazin-1-ylmethyl)-pyridine

HRID 1257124

反応式

HRID 1257124 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:22][C:23]1[N:24]=[CH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2.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.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOC(C)=O>[CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[C:23]([NH:22][C:17]2[CH:16]=[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]3)[CH:20]=[CH:19][N:18]=2)[N:24]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 311869Isoquinolin-3-AmineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866538601-Boc-4-(2-chloropyridin-4-ylmethyl)piperazine

生成物 1

HCID 671756022-(Isoquinolin-3-ylamino)-4-(4-tert-butoxycarbonylpiperazin-1-ylmethyl)-pyridine収率 61%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Boc-4-(2-chloropyridin-4-ylmethyl)piperazine (500 mg, 1.63 mmol) (Preparation B-14) was mixed with 3-aminoisoquinoline (234 mg, 1.0 equiv), Pd2(dba)3 (148 mg, 0.1 equiv), xantphos (140 mg, 0.15 equiv), and Cs2CO3 (735 mg, 1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound (250 mg, yield 61%) was obtained as yellow solid.

後処理

  1. temperatureThe mixture was refluxed overnight
  2. additionto dilute the mixture
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-66314b19fa0d4d94b2096323a4cd1b93
出典データセット
uspto-grants-2013_06
特許番号
US08461339B2

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