Sodium Carbonate → methyl 4-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505809노트

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HRID 505809 반응식
Br[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:5]2[CH:14]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[S:16][C:4]=2[C:3]=1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:9][C:7]([N:6]1[C:2]([C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)=[C:3]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:4]2[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:5]1=2)=[O:8])([CH3:13])([CH3:12])[CH3:11]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 67298537methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

생성물 1

HCID 68467133methyl 4-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 69%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 21863594Toluene ethanol용매

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온도
80 °C

실험 절차

A solution (0.1 M) of methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in EtOH/toluene (1:1) was treated with 4-chlorophenylboronic acid (1.3 eq.) and LiCl (2 eq.). Aqueous Na2CO3 (2 N, 2.5 eq.) was added and the solution was degassed, then Pd(PPh3)4 (0.1 eq.) was added. The mixture was heated to 80° C. for 18 h, then cooled and diluted with AcOEt. The organic phase was washed sequentially with water, aqueous HCl (1 N) and brine, then dried and concentrated giving a residue that was purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether) to afford the title compound (69%) as a solid.

후처리

  1. customthe solution was degassed
  2. temperaturecooled
  3. washThe organic phase was washed sequentially with water, aqueous HCl (1 N) and brine
  4. customdried
  5. concentrationconcentrated
  6. customgiving a residue that
  7. customwas purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether)

출처 및 근거

ORD 기록
ord-23002f57d1f946539406bf88157d8f74
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781431B2

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