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

HRID 505809ノート

反応式

HRID 505809 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-23002f57d1f946539406bf88157d8f74
出典データセット
uspto-grants-2010_08
特許番号
US07781431B2

反応ノート

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