Diisopropylethylamine → HCID 57519384, compound

HRID 1640017Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[Br:17].Br[CH2:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23].C(N(C(C)C)CC)(C)C>C(O)C>[Br:17][C:3]1[CH:4]=[C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][CH2:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 2-(4-amino-3-bromophenyl)propanoate (6.50 g, 21.7 mmol), methyl 2-(bromomethyl)benzoate (4.97 g, 21.7 mmol), diisopropylethylamine (2.80 g, 21.7 mmol), and ethanol (180 mL) was heated at 120° C. in a sealed vial overnight. After cooling to room temperature, the mixture was concentrated and the residue purified by flash chromatography (92:8 hexanes/ethyl acetate) to afford methyl 2-((2-bromo-4-(1-tert-butoxy-1-oxopropan-2-yl)phenylamino)methyl)benzoate (4.72 g, 48%) as thick oil: 1H NMR (500 MHz, CDCl3) δ 7.98 (m, 1H), 7.47 (m, 2H), 7.37-7.31 (m, 2H), 7.01 (dd, J=8.4, 2.0 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 5.03 (br t, J=6.1 Hz, 1H), 4.75 (d, J=6.2 Hz, 2H), 3.92 (s, 3H), 3.43 (q, J=7.2 Hz, 1H), 1.38 (s, 9H), 1.37 (d, J=7.2 Hz, 3H); ESI MS m/z 450 [(M+2)+H]+.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
customthe residue purified by flash chromatography (92:8 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-e505efe5b69d44c0968420bdcc7db78c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110681B2

Reaction notes

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