Sodium Carbonate → HCID 86627906, compound

HRID 1669475Notes

Reaction equation

HRID 1669475 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.[CH:21]([C:23]1[C:24]([O:32][CH3:33])=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=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:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH:21]=[O:22])[C:24]=2[O:32][CH3:33])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateHCID 16218167(3-Formyl-2-methoxyphenyl)boronic acid

Product 1

HCID 86627906HCID 86627906, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPh3)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. 2M Na2CO3 solution (1 eq) was added and the mixture was heated to 110° C. for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1). After evaporation of the fractions containing product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate was obtained as off-white solid (77%). (ES+) m/z 392 (M+H)+.

Workup

  1. customThe solution was degassed
  2. customflushed with Ar
  3. customAll volatiles were evaporated in vacuo
  4. dissolutionthe residual material was dissolved in EtOAc
  5. filtrationfiltered over Celite
  6. customevaporated in vacuo
  7. filtrationThe residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1)
  8. customAfter evaporation of the fractions
  9. additioncontaining product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate

Sources & evidence

ORD record
ord-bfee15f67e3a4700bec296c174cf6635
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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