Boronic Acid → Methyl 3-cyclohexyl-2-(3-formyl-2-thienyl)1H-indole-6-carboxylate

HRID 1444624Notes

Reaction equation

HRID 1444624 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[CH:27]=[CH:26][S:25][C:24]=1B(O)O)=[O:22].[F-].[K+].B(O)O>O1CCOCC1>[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[S:25][CH:26]=[CH:27][C:23]=2[CH:21]=[O:22])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 61668Boronic AcidHCID 522689Potassium Fluoride2×HCID 27734293-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride)HCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 86761056Methyl 3-cyclohexyl-2-(3-formyl-2-thienyl)1H-indole-6-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-bromo-3-cyclohexyl1H-indole-6-carboxylate (prepared as described in published International patent application WO 2004/087714), (3-formyl-2-thienyl)boronic acid (1.2 eq), spray-dried KF (5 eq) and Pd(tBu3P)2 (0.2 eq) were dissolved in dioxane (0.15 M); the reaction mixture was stirred under N2 at RT for 4 h, then more KF, boronic acid and catalyst were added and stirring was continued overnight. All volatiles were evaporated in vacuo and the title compound was isolated by flash chromatography (PE/EtOAc 8:2). Yield 99%; MS (ES+) m/z 368 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customAll volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-06ed445fef2141d59ed7e3685dbebbe7
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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