2-Methyl-2-butene → HCID 71767831, compound

HRID 338224Notes

Reaction equation

HRID 338224 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[C:20](=[CH:22][CH3:23])[CH3:21].Cl([O-])=[O:25].[Na+].[OH2:28].OP([O-])(O)=O.[Na+]>CC#N.C(O)(C)(C)C.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:12])=[O:28])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([C:20]2([OH:25])[CH2:21][CH2:23][CH2:22]2)=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86698575HCID 86698575, compound

Product 1

HCID 71767831HCID 71767831, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 6-fluoro-5-phenyl-1H-indole-3-carbaldehyde (58.0 mg, 0.19 mmol) in MeCN (3 mL), tert-butanol (3 mL) and 2-methyl-2-butene (2 mL, 13.7 mmol) at 0° C. was added a solution of sodium chlorite (253.0 mg, 3.75 mmol) and sodium phosphate monobasic hydrate (585.0 mg, 3.75 mmol) in water (1.5 mL) dropwise. The ice bath was removed and the solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with EtOAc (3×15 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by prep-HPLC (Boston Symmetrix ODS-H 150*30 mm*5 μm; 26-46% MeCN in water (0.225% formic acid); flow rate: 30 mL/min) to afford the title compound (9.5 mg, 16%) as a white solid. MS (ES+) 324.1 (M−H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.13 (br.s., 1H), 11.95 (s, 1H), 8.04-8.06 (m, 2H), 7.60 (d, J=8.40 Hz, 2H), 7.53 (d, J=6.80 Hz, 2H), 7.38 (d, J=11.20 Hz, 1H), 5.56 (s, 1H), 2.42-2.49 (m, 2H), 2.29-2.36 (m, 2H), 1.93-1.98 (m, 1H), 1.68-1.73 (m, 1H).

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe aqueous residue was extracted with EtOAc (3×15 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by prep-HPLC (Boston Symmetrix ODS-H 150*30 mm*5 μm; 26-46% MeCN in water (0.225% formic acid); flow rate: 30 mL/min)

Sources & evidence

ORD record
ord-3bbb23f6cb7846eca77d1e0aba0699ee
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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