5-Bromo-2-nitropyridine → HCID 66818510, compound

HRID 1024791Notes

Reaction equation

HRID 1024791 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:39])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[C:42]1[CH:43]=[CH:44][C:45]([N+:48]([O-:50])=[O:49])=[N:46][CH:47]=1>>[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:39])[C:16]2[CH:17]=[C:18]([O:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:29]=3)[CH:19]=[C:20]([O:22][C:42]3[CH:47]=[N:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 66818915HCID 66818915, compound

Product 1

HCID 66818510HCID 66818510, compoundYield 61.5%

Procedure

Following the procedure of Example 69(b) (4-{3-[4-(tert-Butoxycarbonylamino-methyl)-phenoxy]-5-hydroxy-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl ester 0.4 g (0.72 mmol) and 5-bromo-2-nitro-pyridine (0.17 g, 0.86 mmol) were used to afford 0.3 g of the required product. 1H NMR (DMSO-d6): δ 1.31 (18H, d), 1.8 (4H, d), 3.20 (2H, m), 3.8 (2H, m), 4.1 (2H, d), 7.35 (3H, d), 7.4 (3H, m), 7.9 (1H, d), 8.35 (2H, d), 8.5 (1H, s).

Sources & evidence

ORD record
ord-a5194da21cef41b9973979a931497340
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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