Tert-butyl 4-nitro-2-iodophenylcarbamate → tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamate

HRID 541752Notes

Reaction equation

HRID 541752 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[N:7][CH:8]=1)#[CH:2].I[C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:29][C:28]([NH:27][C:19]1[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=1[C:2]#[C:1][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:6]=[N:7][CH:8]=1)=[O:34])([CH3:33])([CH3:31])[CH3:32]

Participants

3

Reactant 2

HCID 7098713Tert-butyl 4-nitro-2-iodophenylcarbamateHCID 57962286Tert-butyl (5-ethynylpyridin-3-yl)carbamate

Product 1

HCID 57961805tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamateYield 85%

Procedure

This compound was prepared according to the procedure of Example B19 step C, using tert-butyl (5-ethynylpyridin-3-yl)carbamate and tert-butyl (2-iodo-4-nitrophenyl)carbamate as the starting material in 85% yield. LCMS calculated for C23H27N4O6(M+H)+: m/z=455.1.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-f6345892154140cba13c3247c2de47f5
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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