Sodium borohydride → HCID 68865134, compound

HRID 1725908Notes

Reaction equation

HRID 1725908 reaction equation
[Br:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[BH4-].[Na+]>C(O)(C)C>[Br:1][C:2]1[C:11]2[CH:10]=[CH:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68863072HCID 68863072, compound

Product 1

HCID 68865134HCID 68865134, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of Example 103A (150 mg, 0.38 mmol) and NaBH4 (14.3 mg, 0.38 mmol) in isopropanol (3 mL) was heated to reflux overnight and partitioned between diethyl ether and brine. The organic phase was dried (Na2SO4), filtered, concentrated, dissolved in toluene (5 mL), and treated with p-toluenesulfonic acid. The mixture was heated to reflux for 1 hour, cooled to room temperature, and passed through a silica gel plug with dichloromethane to provide the desired product (95 mg, 68% yield). MS (DCI/NH3) m/e 400 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.75 (m, 2H), 7.39 (m, 2H), 7.08 (d, 1H), 6.9 (d, 1H), 6.69 (m, 1H), 6.22 (m, 1H), 2.71 (t, 2H), 2.21 (m, 2H).

Workup

  1. temperatureto reflux overnight
  2. custompartitioned between diethyl ether and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutiondissolved in toluene (5 mL)
  7. additiontreated with p-toluenesulfonic acid
  8. temperatureThe mixture was heated
  9. temperatureto reflux for 1 hour

Sources & evidence

ORD record
ord-e01ae8a3b63843629e5971ccba2252db
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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