Sodium Carbonate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylate

HRID 1713929ノート

反応式

HRID 1713929 の反応式
Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.CCOC(C)=O.[Cl-].[Na+].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:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:34]1[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1)([CH3:28])([CH3:27])[CH3:26]

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 299433152-Bromo-1-tert-butoxycarbonylmethyl-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

生成物 1

HCID 11340537methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylate収率 81%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

A solution (0.1 M) of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (from Step 1) in DME and EtOH (5:2) was treated with 4-methoxyphenylboronic acid (1.5 eq.). Aqueous Na2CO3 (2 N, 8.5 eq.) was added and the solution was degassed, and then heated with Pd(PPh3)4 (0.1 eq.). The mixture was heated at 80° C. for 2 h, then cooled and diluted with EtOAc and brine. The organic phase was separated, dried and concentrated under reduced pressure. The residue was purified by filtration through silica gel (5:95 EtOAc/PE) to give the title compound (81%) as a solid. 1H NMR (300 MHz, DMSO-d6, 300K) δ 1.13-1.38 (m, 3H), 1.33 (s, 9H), 1.61-1.96 (m, 7H), 2.55-2.67 (m, 1H), 3.86 (s, 3H), 3.88 (s, 3H), 4.73 (s, 2H), 7.11 (d, J 8.6, 2H), 7.27 (d, J 8.6, 2H), 7.69 (dd, J 8.4, 1.1, 1H), 7.86 (d, J 8.4, 1H), 8.06 (d, J 1.1, 1H).

後処理

  1. customthe solution was degassed
  2. temperaturecooled
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe residue was purified by filtration through silica gel (5:95 EtOAc/PE)

出典と根拠

ORDレコード
ord-4182c14e3dee4ccda58bf50118c58504
出典データセット
uspto-grants-2010_09
特許番号
US07795250B2

反応ノート

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