Dimethylformamide → HCID 59300484, compound

HRID 603436Notes

Reaction equation

HRID 603436 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C@H:11]([CH2:15][C:16]([O-:18])=O)[CH2:10][CH2:9]2.[CH2:19]([C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([O:33][CH3:34])[CH:27]=2)[O:24][CH:25]=1)[CH3:20].[C:35]([O-])([O-])=O.[Cs+].[Cs+].CN([CH:44]=[O:45])C>O>[CH2:19]([C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[C:8]4[C:12](=[CH:13][CH:14]=3)[C@H:11]([CH2:15][C:16]([O:45][CH2:44][CH3:35])=[O:18])[CH2:10][CH2:9]4)=[C:28]([O:33][CH3:34])[CH:27]=2)[O:24][CH:25]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86644241HCID 86644241, compoundHCID 135974501HCID 135974501, compound

Product 1

HCID 59300484HCID 59300484, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

To a solution of [(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 45) (93.4 mg, 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-9dacea20154e4d068e9d0608c719c8fc
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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