Sodium Carbonate → methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

HRID 1518236Notes

Reaction equation

HRID 1518236 reaction equation
Br[C:2]1[NH:3][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.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.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>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][OH:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 58677008methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylateYield 93%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

A solution (0.04 M) of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in WO2004/087714) in DME/EtOH 5:2 was treated with [2-(hydroxymethyl)phenyl]boronic acid (1.2 eq), Na2CO3 (6 eq) and Pd(PPh3)4 (0.1 eq) at 80° C. After 1 h the mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, then dried and concentrated under reduced pressure. The residue was purified by flash chromatography on SiO2 (7:3 PE/EtOAc) to give the title compound (93%) as a solid. MS (ES+) m/z 364 (M+H+).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on SiO2 (7:3 PE/EtOAc)

Sources & evidence

ORD record
ord-cac3173bf5a44b54a0bd349f98bd7166
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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