4-Nitrophenyl chloroformate → HCID 57431674, compound

HRID 545551Notes

Reaction equation

HRID 545551 reaction equation
Cl.[NH2:2][CH:3]1[CH2:15][CH2:14][C:13]2[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:11]3[CH:10]=[CH:9][C:8]([C:24]#[N:25])=[CH:7][C:6]=3[C:5]=2[CH2:4]1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:28]>>[N+:36]([C:33]1[CH:32]=[CH:31][C:30]([O:29][C:27](=[O:28])[NH:2][CH:3]2[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[C:8]([C:24]#[N:25])[CH:7]=4)[N:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=4)[C:13]=3[CH2:14][CH2:15]2)=[CH:35][CH:34]=1)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 57431673HCID 57431673, compound

Product 1

HCID 57431674HCID 57431674, compoundYield 33%

Procedure

Prepare the title compound by essentially following the procedures as described in Example 162, using 6-amino-9-(3-fluoro-benzyl)-6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile hydrochloride (Preparation 51) and 4-nitrophenyl chloroformate. Purify by silica gel chromatography (50% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes) to give the title compound in 33% yield as a white solid. MS (ES): m/z 346 (M-p-nitrophenolate); HPLC (Method B): Rt=2.23 min (86%).

Workup

  1. customPurify by silica gel chromatography (50% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes)

Sources & evidence

ORD record
ord-6f5bdb1efc7e4c139bf9d418ed9dc920
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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