Benzonitrile, 3-(bromomethyl)- → HCID 66818632, compound

HRID 1024770Notes

Reaction equation

HRID 1024770 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=2[OH:24])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33]>>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:28][C:29]3[CH:36]=[CH:35][CH:34]=[C:31]([C:32]#[N:33])[CH:30]=3)=[CH:19][C:18]=2[O:24][CH2:28][C:29]2[CH:36]=[CH:35][CH:34]=[C:31]([C:32]#[N:33])[CH:30]=2)[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 66818673HCID 66818673, compound

Product 1

HCID 66818632HCID 66818632, compoundYield 67.1%

Procedure

{2-[1-(2,4-Dihydroxy benzoyl)piperidin-4-yl]ethyl}carbamic acid tert-butyl ester (1.05 g, 2.88 mmol) and 3-bromomethyl-benzonitrile (2.25 g, 11.5 mmol) and other reagents as described in Example 75(a) were used to afford 1.15 g of the required product. 1H NMR (DMSO-d6): δ 1.4 (9H, s), 2.1 (2H, d), 2.6 (1H, m), 2.95 (4H, m), 3.45 (1H, m), 4.5 (2H, m), 5.2 (4H, s), 6.7 (2H, d), 6.84 (1H, d), 7.14 (1H, dd), 7.52 (1H, m), 7.62 (3H, d), 7.7 (2H, d), 7.8 (5H, m), 7.95 (1H, s).

Sources & evidence

ORD record
ord-cc96502543604aa38ab5be9d4f66932a
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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