tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate → HCID 66818721, compound

HRID 1024739Notes

Reaction equation

HRID 1024739 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].[C:34]([O:38][C:39](=[O:49])[NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47]Br)=[CH:43][N:42]=1)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:39](=[O:49])[NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][O:22][C:20]2[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]=[C:16]([C:15](=[O:32])[NH:14][CH:11]3[CH2:12][CH2:13][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:33])[CH2:9][CH2:10]3)[CH:21]=2)=[CH:43][N:42]=1)([CH3:37])([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 66818660HCID 66818660, compound

Product 1

HCID 66818721HCID 66818721, compoundYield 81.5%

Procedure

Using 1.2 g (2.65 mmol) of {4-[3-(4-cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester and (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.76 g, 2.65 mmol) and following the procedure of Example 42(b) afforded 1.42 g of the required product. 1HNMR (DMSO-d6): δ 1.25 (4H, m), 1.4 (27H, s), 1.8 (4H, m), 3.20 (1H, m), 3.75 m), 5.25 (2H, s), 6.75 (1H, d), 7.05 (1H, s), 7.15 (2H, d), 7.2 (1H, s), 7.45 (2H, m), 7.85 (2H, d), 7.95 (1H, d), 8.25 (1H, d), 8.5 (1H, s).

Sources & evidence

ORD record
ord-a0a27678a93444adb1b18ea4a4fff5a0
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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