Cesium carbonate → HCID 59300444, compound

HRID 603441Notes

Reaction equation

HRID 603441 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[N:9]=2)[CH:5]=[CH:4][C:3]=1[OH:17].Br[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C@H:28]([C@H:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])[CH2:27][CH2:26]2.C([O-])([O-])=O.[Cs+].[Cs+]>O.CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[N:9]=2)[CH:5]=[CH:4][C:3]=1[O:17][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C@H:28]([C@H:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])[CH2:27][CH2:26]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 59300500HCID 59300500, compoundHCID 136029789HCID 136029789, compound

Product 1

HCID 59300444HCID 59300444, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

2-Methyl-4-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]phenol (57.7 mg, 0.22 mmol), methyl (2S)-2-[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]propanoate (Example 234) (72.0 mg, 0.21 mmol), Cs2CO3 (82.5 mg, 0.25 mmol), and water (3 drops) were combined in DMF (4 mL) and stirred at 40° C. for 16 h. The reaction mixture was concentrated under reduced pressure, water was added and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:20) gave 70 mg (64%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.07 (d, 3H), 1.90 (m, 1H), 2.17 (m, 1H), 2.29 (s, 3H), 2.34 (m, 2H), 2.77-2.91 (m, 3H), 3.50 (m, 1H), 3.71 (s, 3H), 4.17 (t, 2H), 4.25 (t, 2H), 6.70 (d, 1H), 6.78 (s, 1H), 6.92 (d, 1H), 6.99 (d, 1H), 7.79 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc (2×)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:20)

Sources & evidence

ORD record
ord-8501de1ab6fa421e859d278b8f028119
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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