4-Aminocarbonylphenylboronic acid → HCID 59177819, compound

HRID 423482Notes

Reaction equation

HRID 423482 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)=[O:3].Br[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:16][CH:15]=1>>[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)=[CH:18][CH:19]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 27378114-Aminocarbonylphenylboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 59177819HCID 59177819, compoundYield 18.9%

Procedure

The title compound (15 mg, 15%) was prepared from [4-(aminocarbonyl)phenyl]boronic acid (33 mg, 0.2 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol) in a manner similar to Example 21, Step 3 and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.86 (d, 2H, J=8.1 Hz), 7.63 (d, 2H, J=8.1 Hz), 7.55 (d, 2H, J=8.8 Hz), 6.97 (d, 2H, J=8.9 Hz), 6.09 (s, 2H), 4.99-4.86 (m, 1H), 4.28-4.14 (m, 2H), 3.85 (d, 2H, J=6.4 Hz), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.34-1.18 (m, 8H); LRMS (ESI), m/z 419 (M+Na).

Sources & evidence

ORD record
ord-80a9975a6a5b43fc95e0f98b92cec4e3
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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