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2-Methyl-2-butene → 4,6-difluoro-5-[4-(3-hydroxypropoxy)phenyl]-1H-indole-3-carboxylic acid

HRID 338299
Notes
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Reaction equation

HRID 338299 reaction equation
[F:1][C:2]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13][CH:12]=2)=[C:9]([F:22])[CH:8]=[C:7]2[C:3]=1[C:4]([CH:23]=[O:24])=[CH:5][NH:6]2.CC(=CC)C.Cl([O-])=[O:31].[Na+].P([O-])(O)(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[F:1][C:2]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:15][CH:16]=2)=[C:9]([F:22])[CH:8]=[C:7]2[C:3]=1[C:4]([C:23]([OH:31])=[O:24])=[CH:5][NH:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866986434,6-difluoro-5-[4-(3-hydroxypropoxy)phenyl]-1H-indole-3-carbaldehyde

Product 1

HCID 866986454,6-difluoro-5-[4-(3-hydroxypropoxy)phenyl]-1H-indole-3-carboxylic acidYield 43.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22050040Acetonitrile tert-butanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4,6-difluoro-5-[4-(3-hydroxypropoxy)phenyl]-1H-indole-3-carbaldehyde (30 mg, 0.1 mmol) in ACN/t-butanol=1/1(2 mL) was added 2-methyl-2-butene (0.5 mL) and cooled to 0° C. and added the aqueous solution of sodium chlorite (180 mg, 0.5 mL) and sodium dihydrogen phosphate (270 mg, 2 mmol) in water (0.5 mL) dropwise via additional funnel. The reaction was stirred at room temperature for 10 h. The reaction was quenched with sodium sulfite. The mixture was partioned between dichloromethane and water. The combined organics were concentrated to give a residue, which was purified by reverse phase HPLC to give the title compound (15 mg, 43%) as a white solid. MS (AP+) 348.1 (M+H)+. 1H NMR (400 MHz, CD3OD) δ 7.74 (s, 1H), 7.36 (d, 2H), 7.03-6.98 (m, 3H), 4.14 (t, 2H), 3.77 (t, 2H), 2.04-2.01 (m, 2H).

Workup

  1. customThe reaction was quenched with sodium sulfite
  2. concentrationThe combined organics were concentrated
  3. customto give a residue, which
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d72afb6f7e0c4be5a9ab9d5b93bbf68e
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889730B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes