Cesium carbonate → HCID 90414105, compound

HRID 1776733Notes

Reaction equation

HRID 1776733 reaction equation
[CH3:1][C:2]([CH3:30])([CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:17][C:11]=2[N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38](Br)[CH2:39][CH3:40])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]([N:13]2[C:12]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:17][C:11]=3[N:10]=[C:9]2[CH2:8][C:2]([CH3:1])([CH3:30])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:39][CH3:40])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 431414671-Bromo-4-(1-bromopropyl)benzeneHCID 178471314HCID 178471314, compound

Product 1

HCID 90414105HCID 90414105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl 2,2-dimethyl-3-(5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)propanoate) (300 mg, 0.74 mmol), 1-bromo-4-(1-bromopropyl)benzene (413 mg, 1.49 mmol) and cesium carbonate (727 mg, 2.23 mmol) in DMF (3.7 mL) was heated to 100° C. for 3 days. The mixture was cooled and partitioned between water and EtOAc. The organic layer was dried and concentrated to a residue. Purification using FCC afforded the title compound. MS (ESI): mass calcd. for C33H34BrN3O3, 599.18; m/z found, 600.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.14 (d, J=8.5, 1H), 8.05 (d, J=8.5, 1H), 7.83 (d, J=8.2, 1H), 7.74 (ddd, J=8.4, 6.9, 1.4, 1H), 7.62-7.53 (m, 3H), 7.28-7.25 (m, 2H), 6.97-6.92 (m, 3H), 6.62 (d, J=2.3, 1H), 5.38 (dd, J=10.0, 5.9, 1H), 5.34-5.22 (m, 2H), 4.05 (qd, J=7.1, 0.8, 2H), 3.08 (q, J=15.6, 2H), 2.42-2.23 (m, 2H), 1.37 (s, 3H), 1.35 (s, 3H), 1.15 (t, J=7.1, 3H), 0.72 (t, J=7.3, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water and EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated to a residue
  5. customPurification

Sources & evidence

ORD record
ord-2198c6f2f0a14fb0a4881f4805d2efcc
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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