Ethyl bromoacetate → HCID 67357986, compound

HRID 1664490Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:14]([O:21][C:22]([CH:24]1[CH2:36][C:35]2[C:34]3[C:29](=[C:30]([Cl:37])[CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]=2[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:21][C:22]([CH:24]1[CH2:36][C:35]2[C:34]3[C:29](=[C:30]([Cl:37])[CH:31]=[CH:32][CH:33]=3)[N:28]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:27]=2[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Cesium carbonate (6.32 g, 19.2 mmol) and ethyl bromoacetate (1.16 ml, 10.2 mmol) are added to a stirred solution of 8-chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid benzyl ester (2.17 g, 6.4 mmol) in dry DMF (20 ml). The reaction mixture is stirred at 60° C. for 3 h. The precipitate is filtered off and rinsed thoroughly with acetone. The filtrate is concentrated and the residue is purified by flash chromatography on silica gel (heptane/EtOAc 4:1) to afford pure title compound as a yellow solid (2.54 mg) in 93% yield. tR (LC-5) 1.14 min; ESI-MS (positive ion): m/z 426.16 [M+H]+ (calcd 425.91 for C24H24NO4Cl). 1H-NMR (CDCl3): 1.25 (t, J=7.0 Hz, 3H); 2.07 (m, 1H); 2.37 (m, 1H); 2.69 (m, 2H); 2.89 (m, 2H); 3.07 (dd, J=14.4, 4.4 Hz, 1H); 4.22 (q, J=7.3 Hz, 2H); 5.07 (d, J=18.2 Hz, 1H); 5.18 (s, 2H); 5.19 (d, J=18.5 Hz, 1H); 6.97 (t, J=7.9 Hz, 1H); 7.08 (dd, J=7.6, 0.9 Hz, 1H); 7.34 (m, 6H).

Workup

filtrationThe precipitate is filtered off
washrinsed thoroughly with acetone
concentrationThe filtrate is concentrated
customthe residue is purified by flash chromatography on silica gel (heptane/EtOAc 4:1)

Sources & evidence

ORD record: ord-8fbab489b0244badb8965d265286fe01
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039474B2

Reaction notes

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