2-Methyl-2-butene → HCID 86698621, compound

HRID 1054617Notes

Reaction equation

HRID 1054617 reaction equation
[Cl: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][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:34].[Na+].OP([O-])(O)=O.[Na+]>C(#N)C.O.C(O)(C)(C)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:34])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86698620HCID 86698620, compound

Product 1

HCID 86698621HCID 86698621, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 6-chloro-5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1H-indole-3-carbaldehyde (130 mg, 0.34 mmol) in acetonitrile (4 mL) was added tert-butanol (4 mL), water (4 mL) and 2-methyl-2-butene (2.76 mL). After stirred for 2 min, sodium chlorite (680 mg, 10.15 mmol) and sodium phosphate monobasic (1.59 mg, 10.19 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 16 hours. The reaction was quenched with sodium sulfite and the mixture was concentrated in vacuo to give a residue, which was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×15 mL), dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by prep-HPLC to give 6-chloro-5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1H-indole-3-carboxylic acid (30 mg, 22%) as a yellow solid. MS (ES+) 401.1 (M+H)+. 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 8.02 (s, 1H), 7.98 (s, 1H) 7.57 (s, 1H), 7.39 (d, 2H), 7.04 (d, 2H), 4.31 (m, 2H), 3.83 (m, 4H), 3.17 (m, 2H), 2.96 (m, 4H).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. customThe reaction was quenched with sodium sulfite
  3. concentrationthe mixture was concentrated in vacuo
  4. customto give a residue, which
  5. extractionwas extracted with ethyl acetate (3×10 mL)
  6. washThe combined organic layers were washed with brine (2×15 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto give a residue, which
  10. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-993286b37dd84a86acf632e1bba67733
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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