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Sodium Carbonate → 3-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1047529
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Reaction equation

HRID 1047529 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](Br)[CH:17]=2)[N:12]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:11]=1.[CH3:26][S:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:29])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH:35]=3)[CH:17]=2)[N:12]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 1363522433-(1H-benzo[d]imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 1363522463-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Yield 22.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (30 mg, 0.0755 mmol), 3-(methylsulfonyl)phenyl boronic acid (15 mg, 0.075 mmol) and triphenylphosphine (2 mg, 0.007 mmol) were dissolved in a mixture of THF (6 mL), and 1M sodium carbonate (8 mg, 0.075 mmol) and palladium (II) acetate (2 mg, 0.009 mmol) were added. The solution was heated overnight at reflux. After cooling to room temperature, the solvent was removed in vacuo, the residue was dissolved in ethyl acetate (20 mL), and washed with water (10 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine (25 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound (8 mg) as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.93 (s, 1H), 8.83 (s, 1H), 8.19 (s, 1H), 7.97 (d, 1H, J=8.0 Hz), 7.86 (m, 2H), 7.61 (t, 1H, J=7.6 Hz), 7.45 (m, 1H), 7.24 (m, 4H), 5.77 (dd, 1H, J=2.4 and 9.6 Hz), 4.04 (m, 1H), 3.75 (m, 1H), 3.07 (s, 3H), 2.59 (m, 1H), 2.12 (m, 2H), 1.76 (m, 3H); ESI-MS [M+H]+: 473.3.

Workup

  1. additionwere added
  2. temperatureThe solution was heated overnight
  3. temperatureat reflux
  4. customthe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  6. washwashed with water (10 mL)
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
  9. washThe combined organic layers were washed with brine (25 mL)
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customPurification by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1fa1c05261344330ad3aa00b4a6e482b
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569511B2

Reaction notes

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