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Potassium Carbonate → tert-butyl 5-bromo-3-(quinolin-3-yl)-1H-indole-1-carboxylate

HRID 634147
Notes
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Reaction equation

HRID 634147 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2I.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21](B(O)O)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>O1CCOCC1.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.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2[C:21]1[CH:20]=[N:19][C:28]2[C:23]([CH:22]=1)=[CH:24][CH:25]=[CH:26][CH:27]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734663Quinoline-3-boronic acidHCID 17749978tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate

Product 1

HCID 68327989tert-butyl 5-bromo-3-(quinolin-3-yl)-1H-indole-1-carboxylateYield 36.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate (1.750 g, 4.146 mmol, synchem), 3-quinolineboronic acid (1.076 g, 6.22 mmol), Pd(PPh3)4 (0.240 g, 0.207 mmol) and potassium carbonate ((1.719 g, 12.439 mmol) in dioxane (3.0 mL) was added H2O (1.0 mL) and the reaction was heated at 60° C. for 42 h. Saturated NaHCO3 solution (5.0 mL) was added to the mixture. The resulting mixture was extracted with EtOAc. The organic phases were combined, dried with sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give tert-butyl 5-bromo-3-(quinolin-3-yl)-1H-indole-1-carboxylate (642 mg, 36.6%) as a white foam. MS (ESI, pos. ion) m/z: 423 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.68 (s, 9H), 7.62 (dd, J=8.8, 1.8 Hz, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.79 (t, J=7.3 Hz, 1H), 8.07 (d, J=8.5 Hz, 1H), 8.13-8.20 (m, 3H), 8.30 (s, 1H), 8.74 (d, J=1.5 Hz, 1H), 9.26 (d, J=2.0 Hz, 1H)

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-50843f9ab0d74475a693b699815508de
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes