4-Ethoxycarbonylphenylboronic acid → ethyl 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoate

HRID 38010Notes

Reaction equation

HRID 38010 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:29]=1)[N:7]=[C:8]([NH:21]C(=O)OC(C)(C)C)[CH2:9][C:10]([C:12](=[O:20])[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[CH:11]2.[CH2:30]([O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)=[O:34])[CH3:31]>>[NH2:21][C:8]1[CH2:9][C:10]([C:12](=[O:20])[N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])=[CH:11][C:5]2[CH:4]=[CH:3][C:2]([C:38]3[CH:39]=[CH:40][C:35]([C:33]([O:32][CH2:30][CH3:31])=[O:34])=[CH:36][CH:37]=3)=[CH:29][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27343504-Ethoxycarbonylphenylboronic acidHCID 46928349tert-Butyl (8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-yl)carbamate

Product 1

HCID 51033749ethyl 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoate

Procedure

The title compound was prepared by the procedures as described in Example 124 (Step F) and Example 101 (Step I) using tert-butyl (1E,4E)-8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate and 4-(ethoxycarbonyl)phenylboronic acid. MS APCI (+) m/z 434 (M+1) detected; 1H-NMR (400 MHz, CDCl3) δ 8.11 (d, 2H), 7.72 (d, 2H), 7.54 (d, 1H), 7.38 (d, 1H), 7.34 (dd, 1H), 6.84 (s, 1H), 4.40 (q, 2H), 3.47 (br s, 4H), 2.83 (s, 2H), 1.62-1.72 (m, 4H), 1.42 (t, 3H), 0.94 (t, 6H).

Sources & evidence

ORD record
ord-0ddc0afd33e4479dbda0c657517984bc
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

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