2-Bromo-5-bromomethylpyridine → HCID 86665958, compound

HRID 1024738Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41]Br)=[CH:37][N:36]=1>>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:17]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:19]=[C:20]([O:22][CH2:41][C:38]3[CH:37]=[N:36][C:35]([Br:34])=[CH:40][CH:39]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 64246602-Bromo-5-bromomethylpyridine

HCID 66818660HCID 66818660, compound

Product 1

HCID 86665958HCID 86665958, compoundYield 77.9%

Procedure

Using 1.4 g (3.1 mmol) of {4-[3-(4-cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester and 2-bromo-5-bromomethyl-pyridine (0.77 g, 3.1 mmol) and following the procedure of Example 42(b) afforded 1.5 g of the required product. 1H NMR (DMSO-d6): δ 1.20 (4H, m), 1.40 (9H, s), 1.80 (4H, m), 3.2 (1H, m), 3.70 (1H, m), 5.25 (2H, s), 6.75 (1H, d), 7.0 (1H, s), 7.15 (2H, d), 7.22 (1H, s), 7.45 (1H, s), 7.7 (1H, d), 7.85 (3H, m), 8.3 (1H, d), 8.5 (1H, s).

Sources & evidence

ORD record: ord-25484b94222f429782bd4f9c0001a394
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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