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

HRID 1054569Notes

Reaction equation

HRID 1054569 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-38a12e9b7e254bb894b41b7174c9d4c0
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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