Sodium borohydride → HCID 12150687, compound

HRID 2086168Notes

Reaction equation

HRID 2086168 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24](=[O:32])[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:18]=1)=[C:10]([CH3:33])[CH:9]=2)=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:24]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[OH:32])[CH:18]=1)=[C:10]([CH3:33])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12150688HCID 12150688, compound

Product 1

HCID 12150687HCID 12150687, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[3-(4-Fluoro-benzoyl)-4-hydroxy-phenoxy]-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (20 mg, 0.045 mmol) in ethanol (1 mL) at room temperature was added sodium borohydride (3.4 mg, 0.089 mmol), and the resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with 1M HCl.(10 mL), diluted with ethyl acetate (10 mL). The ethyl acetate layer was separated, washed with 1M HCl (2 times 10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride) to afford the title compound (17.5 mg) as a solid. 1H NMR (400 MHz, CDCl3) δ8.76 (s, 1H), 7.31-7.23 (m, 2H), 7.17 (s, 1H), 7.05 (s, 1H), 6.98 (t, 2H), 6.72 (d, 1H), 6.50 (dd, 1H), 6.36 (d, 1H), 5.84 (s, 1H), 4.40-4.34 (q, 2H), 2.25 (s, 3H), 2.14 (s, 3H), 1.38 (t, 3H). MS (APCI−) Calc:449.2, Found: 448.3 (M−1).

Workup

  1. customThe reaction was quenched with 1M HCl
  2. addition(10 mL), diluted with ethyl acetate (10 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with 1M HCl (2 times 10 mL), brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride)

Sources & evidence

ORD record
ord-d79aa14ea0ae4d57b4dec8d27c5889b2
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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