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Potassium Carbonate → 5'-(3-Chlorophenyl)-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazol]-4''-amine

HRID 539352
Notes
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Reaction equation

HRID 539352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[CH:14][C:15]2[O:26][C:25]3([CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28][CH2:27]3)[C:18]3([N:22]=[C:21]([NH2:23])[C:20]([CH3:24])=[N:19]3)[C:16]=2[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.Cl[Pd-]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]3[O:26][C:25]4([CH2:27][CH2:28][CH:29]([O:32][CH3:33])[CH2:30][CH2:31]4)[C:18]4([N:22]=[C:21]([NH2:23])[C:20]([CH3:24])=[N:19]4)[C:16]=3[CH:17]=2)[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 679795525'-Bromo-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazol]-4''-amine2×

Product 1

HCID 679793635'-(3-Chlorophenyl)-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazol]-4''-amineYield 47%

Reagents, catalysts & solvents 2

HCID 178479795
HCID 178479795, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

3-Chlorophenylboronic acid (47.7 mg, 0.31 mmol), 5′-bromo-4-methoxy-5″-methyldispiro-[cyclohexane-1,2′-[1]benzofuran-3′,2″-imidazol]-4″-amine (Example 29, 77 mg, 0.20 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(I) (8.37 mg, 10.18 μmol) were put in a microwave vial and dissolved in dry dioxane (2 mL). A 2M aq. solution of K2CO3 (0.204 mL, 0.41 mmol) was added, the mixture was degassed with nitrogen gas and the mixture was heated at 120° C. for 20 min in a microwave reactor. The mixture was combined with a second reaction from 10 mg (0.03 mmol) of 5′-bromo-4-methoxy-5″-methyldispiro[cyclohexane-1,2′-[1]benzofuran-3′,2″-imidazol]-4″-amine and concentrated. EtOAc (7 mL) and a sat. aq. solution of NaHCO3 (5 mL) was added and the phases were separated. The aqueous phase was extracted with EtOAc (5 mL) and the combined organic layers were dried over MgSO4, filtered and evaporated. The crude product was purified by preparative chromatography, yielding 38.5 mg of the title compound (41% yield). 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.21 (m, 1 H), 1.46 (m, 3 H), 1.82 (m, 2 H), 1.98 (m, 2 H), 2.21 (s, 3 H), 3.09 (m, 1 H), 3.22 (s, 3 H), 6.71 (br. s., 2 H), 6.85 (d, 1 H), 6.98 (d, 1 H), 7.32 (m, 1 H), 7.40 (s, 1 H), 7.47 (m, 1 H), 7.51 (m, 1 H), 7.54 (s, 1 H); MS (APCI+) m/z 410 [M+H]+.

Workup

  1. customthe mixture was degassed with nitrogen gas
  2. concentrationconcentrated
  3. additionEtOAc (7 mL) and a sat. aq. solution of NaHCO3 (5 mL) was added
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with EtOAc (5 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by preparative chromatography

Sources & evidence

ORD record
ord-2e8f2ad426ff485c9394297ba2b37876
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865911B2

Reaction notes

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