Dichloromethane → HCID 44197664、化合物

HRID 1970944ノート

反応式

HRID 1970944 の反応式
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22](B4OC(C)(C)C(C)(C)O4)[CH:23]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:33][C:34]1[CH:39]=[C:38](Cl)[N:37]=[C:36]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[N:35]=1.C(Cl)Cl>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:33][C:34]1[N:35]=[C:36]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[N:37]=[C:38]([C:22]2[CH:23]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]4)=[O:11])=[CH:13][CH:14]=3)[CH:19]=[N:20][CH:21]=2)[CH:39]=1

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 120574654,6-dichloro-2-(2-pyridinyl)pyrimidineHCID 68754506HCID 68754506、化合物

生成物 1

HCID 44197664HCID 44197664、化合物

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

A solution of (4-Isopropylpiperazin-1-yl)(4-(5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)pyridin-3-yl)-phenyl)-methanone (Int. I) (1.5 eq, 402 mg) in DME (1 ml) and 2M sodium carbonate (0.62 ml) is treated with 4,6-dichloro-2-pyridin-2-yl-pyrimidine (Int. C) (1 eq, 139 mg) and placed under an atmosphere of argon. PdCl2(dppf).DCM (0.1 eq. 45 mg) is added and the reaction mixture is heated using microwave radiation at 90° C. for 90 minutes. After cooling to room temperature, the mixture is partitioned between DCM/water and the organic portion is separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue is purified by chromatography on silica eluting with 0-10% MeOH in DCM to afford the title compound [M+H]+=499/501 as a solid.

後処理

  1. temperaturethe reaction mixture is heated
  2. customat 90° C.
  3. customfor 90 minutes
  4. customthe mixture is partitioned between DCM/water
  5. customthe organic portion is separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue is purified by chromatography on silica eluting with 0-10% MeOH in DCM

出典と根拠

ORDレコード
ord-7d860ff69b4042a9bfc18037fbcac467
出典データセット
uspto-grants-2013_04
特許番号
US08431578B2

反応ノート

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