Sodium Carbonate → HCID 69157497, 화합물

HRID 1294391노트

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HRID 1294391 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 69157497HCID 69157497, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 20197112Isopropanol dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7758adbfb2fb40888306503446f978c7
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238706B2

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