Dimethylformamide → (1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 872355ノート

反応式

HRID 872355 の反応式
CN(C=O)C.[C:6]([O:10][C:11](=[O:47])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]4[CH:30]=[CH:29][C:28](B5OC(C)(C)C(C)(C)O5)=[CH:27][N:26]4[C:40]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].[CH2:48]([O:55][C:56]1[C:61](Br)=[CH:60][CH:59]=[CH:58][N:57]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[C:6]([O:10][C:11](=[O:47])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]4[CH:30]=[CH:29][C:28]([C:61]5[C:56]([O:55][CH2:48][C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=6)=[N:57][CH:58]=[CH:59][CH:60]=5)=[CH:27][N:26]4[C:40]=3[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH2:16]1)([CH3:8])([CH3:7])[CH3:9]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 147124562-Benzyloxy-3-bromopyridineHCID 66665620(1-{4-[3-Phenyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

生成物 1

HCID 66665949(1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To the crude DMF solution of the boronate from Step 1 was added 2-benzyloxy-3-bromopyridine (0.25 g), aqueous sodium carbonate solution (2M, 2.8 mL) and dioxane (4 mL) and the mixture placed under argon. [1,1-bis-(diphenylphosphino)-ferrocene]-dichloropalladium-dichlormethane-complex (0.070 mg) was added and the mixture heated at 110° C. under microwave irradiation for 30 minutes. On cooling the mixture was partitioned between DCM and water and extracted. The organic portion was washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography on silica gel to give the title compound (138 mg).

後処理

  1. temperatureOn cooling the mixture
  2. customwas partitioned between DCM and water
  3. extractionextracted
  4. washThe organic portion was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customPurification

出典と根拠

ORDレコード
ord-f68346fadb04410eb661446e52b9d0fc
出典データセット
uspto-grants-2015_03
特許番号
US08975265B2

反応ノート

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