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Toluene → HCID 86698714, compound

HRID 1054714
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Reaction equation

HRID 1054714 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.Cl.Br[C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:34][CH2:33][NH:32]2)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.C(O)C>[NH:32]1[CH2:33][CH2:34][CH:31]1[C:28]1[CH:29]=[CH:30][C:25]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][C:2]=2[Cl:1])[NH:8][CH:7]=[C:6]3[C:11]([O:13][CH3:14])=[O:12])=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 866987152-(4-bromophenyl)azetidine hydrochloride

Product 1

HCID 86698714HCID 86698714, compoundYield 379.6%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalyst
HCID 702EthanolSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 6-Chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-1H-indole-3-carboxylate (50 mg, 0.16 mmol), 2-(4-bromophenyl)azetidine hydrochloride (400 mg, 1.24 mmol), 2M aqueous potassium carbonate (3.11 mL, 6.22 mmol), toluene (9 mL), and ethanol (3 mL) was sparged with nitrogen for 10 minutes, then treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (46 mg, 0.056 mmol). The reaction mixture was heated to 100° C. and stirred. After 2 hours the reaction was cooled to room temperature, diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil, which was purified by flash chromatography (40 g silica, 0-40% methanol/ethyl acetate (1% TEA modifier), 24 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a yellow solid (207 mg, 49% yield). MS (ES+) 341.2 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.98 (d, J=3.90 Hz, 2 H), 7.56 (s, 1 H), 7.41 (s, 4 H), 5.02 (t, J=8.17 Hz, 1 H), 3.84 (s, 3 H), 3.68-3.79 (m, 1 H), 3.34-3.45 (m, 1 H), 2.47-2.66 (m, 2 H).

Workup

  1. customwas sparged with nitrogen for 10 minutes
  2. temperatureAfter 2 hours the reaction was cooled to room temperature
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil, which
  8. customwas purified by flash chromatography (40 g silica, 0-40% methanol/ethyl acetate (1% TEA modifier), 24 column volumes)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe478e1ef4e447daba58bf47073cf1b4
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394285B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes