Ethyl 2-bromopropionate → HCID 20640424, compound

HRID 1532347Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH:5]=[C:4]1[CH2:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([C@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1)=[O:22])[CH3:2].C([N:31](C(C)C)CC)(C)C.Br[CH:38]([CH3:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40]>C(#N)C>[CH2:42]([O:41][C:39](=[O:40])[CH:38]([N:24]1[CH2:25][CH2:26][CH2:27][C@@H:23]1[C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[CH2:15][CH2:14][C:4]1[N:3]([CH2:1][CH3:2])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([C:12](=[NH:31])[NH2:13])[CH:10]=2)=[O:22])[CH3:44])[CH3:43]

Participants

Conditions

Temperature: 70 °C

Procedure

300 mg (0.823 mmole) of 1-ethyl-2-[2-[(S)-1-[((R)-pyrrolidin-2-yl)carbonyl]pyrrolidin-2-yl]ethyl]indole-6-carbonitrile was dissolved in 15 ml of acetonitrile, and 0.29 ml (1.646 mmole) of diisopropylethylamine and 0.22 ml (1.646 mmole) of ethyl 2-bromopropionate were added thereto. The reaction mixture was heated to 70° C., stirred for 4 hours, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol(20:1)] to obtain 310 mg of the title compound as a pale yellow oil.

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol(20:1)]

Sources & evidence

ORD record: ord-a7523a3a37964479963dc6e61b63b552
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201006B1

Reaction notes

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