Sodium borohydride → HCID 21084550, compound

HRID 347941Notes

Reaction equation

HRID 347941 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][OH:24])=[CH:21][CH:22]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 21084549HCID 21084549, compound

Product 1

HCID 21084550HCID 21084550, compoundYield 51%

Procedure

N-Benzyl-3-(4-formylphenyl)indole (9) and NaBH4 are allowed to react in the same manner as described above in the preparation of compound 7 to afford compound 10 in 51% yield. mp 122° C.; IR (cm−1): 3462, 1742; 1H NMR (CDCl3): δ 7.94–7.97 (m, 1H), 7.64–7.68 (d, 3H), 7.41–7.45 (d, 10H), 5.34 (s, 2H), 4.72 (s, 2H). HRMS: m/z 313.1466 (calculated for C22H19NO, 313.1467).

Workup

  1. customto react in the same manner

Sources & evidence

ORD record
ord-d54f375281a54dd786a299c5c6f86533
Source dataset
uspto-grants-2007_02
Patent number
US07176230B2

Reaction notes

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