Cesium carbonate → HCID 59300484, compound

HRID 2235905Notes

Reaction equation

HRID 2235905 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C@H:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18]Br)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].[CH2:21]([C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([O:35][CH3:36])[CH:29]=2)[O:26][CH:27]=1)[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH2:21]([C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:18][CH2:17][CH2:16][O:15][C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][CH:12]=3)[C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH2:7][CH2:8]4)=[C:30]([O:35][CH3:36])[CH:29]=2)[O:26][CH:27]=1)[CH3:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 16110497ethyl[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetateHCID 135974501HCID 135974501, compound

Product 1

HCID 59300484HCID 59300484, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of [(1S-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 45) (93.4mg, 0.274 mmol) and 4-(4-ethyl-1,3-oxazol-2-yl)-2-methoxyphenol (40.0 mg, 0.182 mmol) (Example 172) in DMF (4 mL) was added Cs2CO3 (118.9 mg, 0.365 mmol) and water (4 drops). The reaction mixture was stirred at rt for 16 h, then filtered, and the filtrate concentrated under reduced pressure. Purification by preparative HPLC (acetonitrile/water (v/v)=1:1 to 9:1 gradient) gave 73.6 mg (84%) of the title compound as an off-white solid. 1H NMR (400 MHz, CD2Cl2) δ 7.57 (d, 2H), 7.41 (s, 1H), 7.05 (d, 1H), 6.98 (d, 1H), 6.80 (s, 1H), 6.72 (d, 1H), 4.25 (t, 2H), 4.17 (m, 4H), 3.93 (s, 3H), 3.51 (m, 1H), 2.85 (m, 2H), 2.71 (dd, 1H), 2.62 (q, 2H), 2.40 (m, 2H), 2.31 (t, 2H), 1.76 (m, 1H), 1.29 (m, 6H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customPurification by preparative HPLC (acetonitrile/water (v/v)=1:1 to 9:1 gradient)

Sources & evidence

ORD record
ord-fedf2ac801ab4413814bd3201fbc7d9a
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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