Sodium borohydride → 3-Cyano-1-[hydroxy-(4-imidazol-1-yl-phenyl)-methyl]-pyrrolo[1,2-a]quinoline

HRID 720417Notes

Reaction equation

HRID 720417 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[CH:26][N:25]=[CH:24]3)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]([OH:28])[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[CH:26][N:25]=[CH:24]3)=[CH:21][CH:22]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 218921063-Cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinoline

Product 1

HCID 102482043-Cyano-1-[hydroxy-(4-imidazol-1-yl-phenyl)-methyl]-pyrrolo[1,2-a]quinolineYield 95.8%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 3-cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinoline (40 mg, 0.11 mmol) in 1:1 methanol/chloroform (10 mL) was added sodium borohydride portion-wise over 1 h and the reaction mixture was stirred overnight. It was worked up as described in Example 22 and the crude was purified by chromatography (5% methanol/chloroform) to yield the title compound (38.4 mg, 95%). 1H NMR (CDCl3/MeOH-d4): 8.80 (d, J=8.7 Hz, 1H), 7.93 (s, 1H), 7.80 (dd, J=7.8, 1.5 Hz, 1H), 7.53 (m, 8H), 7.38 (t, J=1.2 Hz, 1H), 7.12 (s, 1H), 6.57 (s, broad, 2H).

Workup

  1. customthe crude was purified by chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-5f0bf5edad7544559e51c371a1383042
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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