2-Methyl-2-butene → HCID 86698770, compound

HRID 1054780Notes

Reaction equation

HRID 1054780 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]([C:19]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:31].[Na+].O.O.P([O-])(O)(O)=O.[Na+]>CC#N.O.C(O)(C)(C)C>[C:22]([C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][C:2]=3[Cl:1])[NH:8][CH:7]=[C:6]4[C:11]([OH:31])=[O:12])=[CH:14][CH:15]=2)[CH2:20][CH2:21]1)([OH:24])=[O:23]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86698769HCID 86698769, compound

Product 1

HCID 86698770HCID 86698770, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]cyclopropanecarboxylic acid (253 mg, 0.577 mmol) was dissolved in MeCN (6 mL) and warm t-butanol (6 mL). 2-methyl-2-butene (4 mL) was added and the mixture was cooled to 0° C. Sodium chlorite (780 mg, 11.6 mmol) and sodium dihydrogen phosphate dihydrate (1800 mg, 11.54 mmol) were dissolved in water (4 mL). The aqueous solution was added to the organic solution dropwise via addition funnel and the ice bath was removed and the mixture was allowed to warm to room temperature overnight. The reaction was concentrated to remove the organics and extracted with ethyl acetate (20 mL×3). The combined organics were washed with brine (20 mL), dried and concentrated and then purified by reverse phase HPLC to give the title compound (62.4 mg, 30.5% yield) as a white solid. MS (AP+) 377.9 (M+Na)+. 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.40 (m, 4H), 1.61 (m, 2H), 1.27 (m, 2H).

Workup

  1. additionThe aqueous solution was added to the organic solution dropwise via addition funnel
  2. customthe ice bath was removed
  3. temperatureto warm to room temperature overnight
  4. concentrationThe reaction was concentrated
  5. customto remove the organics and
  6. extractionextracted with ethyl acetate (20 mL×3)
  7. washThe combined organics were washed with brine (20 mL)
  8. customdried
  9. concentrationconcentrated
  10. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-1938bad2f4bf4d9c8829c172f3a16ea9
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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