1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine

HRID 1924984

反応式

HRID 1924984 の反応式
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[N:12]1([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC([O-])(C)C.[Na+].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>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]>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[CH:23][N:22]=2)=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 113673465-Morpholinopyridin-2-amineHCID 23676156Sodium t-butoxideHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

生成物 1

HCID 59023091(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

In the same way as described for compound 90, step 1, using 5,8-dibromo-imidazo[1,2-a]pyrazine (0.4 g, 1.45 mmol), 5-morpholin-4-yl-pyridin-2-ylamine (0.258 g, 1.23 mmol), NaOtBu (0.19 g, 2.04 mmol), Pd2dba3 (0.053 g, 0.058 mmol) and Xantphos (0.067 g, 0.116 mmol) in toluene (6 mL). After removing the solvent in vacuo, the mixture is purified by silica gel column chromatography eluting with 1:4 petroleum ether:ethyl acetate followed by 99:1 DCM:NH3 (7M in MeOH). The title compound is isolated (216.4 mg, 47%). LCMS: Rt 2.16 min (93.2%).

後処理

  1. customAfter removing the solvent in vacuo
  2. customthe mixture is purified by silica gel column chromatography
  3. washeluting with 1:4 petroleum ether

出典と根拠

ORDレコード
ord-518cd8d641454056963ce5bb3470f5b7
出典データセット
uspto-grants-2012_05
特許番号
US08178530B2

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