Sodium Carbonate → HCID 69157497、化合物

HRID 1294391ノート

反応式

HRID 1294391 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[C:4]([F:15])[CH:3]=1.[F:16][C:17]([F:49])([F:48])[CH2:18][NH:19][C:20]([C:22]1[C:31](=[O:32])[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35](B3OC(C)(C)C(C)(C)O3)[CH:34]=2)[CH:23]=1)=[O:21].CN(C)C1C=CC=CC=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CC(O)C.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]>[F:15][C:4]1[CH:3]=[C:2]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([N:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][N:26]=4)[C:31](=[O:32])[C:22]([C:20]([NH:19][CH2:18][C:17]([F:48])([F:49])[F:16])=[O:21])=[CH:23]3)[CH:34]=2)[CH:7]=[CH:6][C:5]=1[CH:8]1[CH2:10][CH:9]1[C:11]([O:13][CH3:14])=[O:12]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 69157593(+)-Methyl 2-(4-bromo-2-fluorophenyl)cyclopropanecarboxylateHCID 69159248HCID 69159248、化合物

生成物 1

HCID 69157497HCID 69157497、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 20197112Isopropanol dimethylformamide溶媒

実験手順

To a solution of (+)-methyl 2-(4-bromo-2-fluorophenyl)cyclopropanecarboxylate from step 8 (1.2 eq) and boronate ester from step 4 (1 eq) in DMF-iPrOH (1:1, 0.1M), was added tris(dibenzylideneacetone)dipalladium(0) (0.055 eq), 2-(dimethylamino)-2′-(dicyclohexylphosphino)biphenyl (0.13 eq) and a sodium carbonate solution (2M, 4 eq) The reaction mixture was heated at 78° C. for 2 h. The reaction mixture was filtered on Celite and silica gel (1:1) and washed with EtOAc. The filtrate was concentrated in vacuo and remaining solvents were distilled in vacuo. The resulting yellow solid is stirred vigourously in ether. The residue then isolated by filtration and washed with ether. Mother liquors were further purified by flash chromatography (toluene/EtOAc, 100:0 to 70:30).

後処理

  1. filtrationThe reaction mixture was filtered on Celite and silica gel (1:1)
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. distillationwere distilled in vacuo
  5. customThe residue then isolated by filtration
  6. washwashed with ether
  7. customMother liquors were further purified by flash chromatography (toluene/EtOAc, 100:0 to 70:30)

出典と根拠

ORDレコード
ord-7758adbfb2fb40888306503446f978c7
出典データセット
uspto-grants-2007_07
特許番号
US07238706B2

反応ノート

読み込み中…