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

HRID 1713929노트

반응식

HRID 1713929 반응식
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]

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4182c14e3dee4ccda58bf50118c58504
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795250B2

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