Sodium borohydride → HCID 22467219, compound

HRID 381334Notes

Reaction equation

HRID 381334 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH:35]=[O:36])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1>C(O)C>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][OH:36])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:13]([NH:15][S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:18])=[O:17])=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22467241HCID 22467241, compound

Product 1

HCID 22467219HCID 22467219, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (51 mg, 1.33 mmol) was added to a stirred solution of 3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-6-bromo-1-methyl-1H-indole (from Example 94, 305 mg, 0.66 mmol) in ethanol (10 ml) at room temperature under a nitrogen atmosphere. After 1 h the ethanol was removed in vacuo and the product was extracted from 0.5 N hydrochloric acid (50 ml) with dichloromethane (2×50 ml). The organic layers were dried (MgSO4) and concentrated. Flash column chromatography (elution with 95% dichloromethane/5% methanol) gave the product (230 mg) as a white foam.

Workup

  1. customAfter 1 h the ethanol was removed in vacuo
  2. extractionthe product was extracted from 0.5 N hydrochloric acid (50 ml) with dichloromethane (2×50 ml)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. washFlash column chromatography (elution with 95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-bfb97308d2b3491bb312dd432d5cf48d
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

Loading…