Dichloromethane → HCID 44197664, 화합물

HRID 1970944노트

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HRID 1970944 반응식
[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

참가 물질

7

반응물 3

HCID 6344DichloromethaneHCID 120574654,6-dichloro-2-(2-pyridinyl)pyrimidineHCID 68754506HCID 68754506, 화합물

생성물 1

HCID 44197664HCID 44197664, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d860ff69b4042a9bfc18037fbcac467
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431578B2

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