4-(Adamantan-1-ylmethoxy)-3-bromobenzonitrile → 4-(Adamantan-1-ylmethoxy)-3-bromobenzamide

HRID 1849505Notes

Reaction equation

HRID 1849505 reaction equation
C12(C[O:12]C3C=CC(C#N)=CC=3C3C(OC)=NC=CC=3)CC3CC(CC(C3)C1)C2.[C:29]12([CH2:39][O:40][C:41]3[CH:48]=[CH:47][C:44]([C:45]#[N:46])=[CH:43][C:42]=3[Br:49])[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2>>[C:29]12([CH2:39][O:40][C:41]3[CH:48]=[CH:47][C:44]([C:45]([NH2:46])=[O:12])=[CH:43][C:42]=3[Br:49])[CH2:30][CH:31]3[CH2:37][CH:35]([CH2:34][CH:33]([CH2:32]3)[CH2:38]1)[CH2:36]2

Participants

3

Reactant 2

HCID 867028434-(Adamantan-1-ylmethoxy)-3-bromobenzonitrileHCID 867028444-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile

Product 1

HCID 867028504-(Adamantan-1-ylmethoxy)-3-bromobenzamide

Procedure

Following the procedure as described in Example 38 step 3 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile with 4-(adamantan-1-ylmethoxy)-3-bromobenzonitrile, the title compound was obtained as a colorless solid (1.80 g, 98%): 1H NMR (300 MHz, CDCl3) δ 7.99-7.97 (m, 1H), 7.74-7.69 (m, 1H), 6.87-6.83 (m, 1H), 5.86 (br s, 2H), 3.57 (s, 2H), 2.02 (br s, 3H), 1.79-1.58 (m, 12H); MS (ES+) m/z: 364.1, 366.1 (M+1).

Sources & evidence

ORD record
ord-9822254a1e2247e0a622b7e1d4ddb614
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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