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Potassium Carbonate → (S)-benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 42997
Notes
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Reaction equation

HRID 42997 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20]O)[CH:17]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[F:33][C:34]([F:43])([F:42])[C:35]1[C:39]([CH2:40][OH:41])=[CH:38][NH:37][N:36]=1>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][N:37]3[CH:38]=[C:39]([CH2:40][OH:41])[C:35]([C:34]([F:33])([F:42])[F:43])=[N:36]3)[CH:17]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 70224068(S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamateHCID 178519885HCID 178519885, compound

Product 1

HCID 68364703(S)-benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-ylcarbamateYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

(S)-benzyl-5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate (7.13 mmol, 2.12 g) was dissolved in DCM (20 mL), thionyl chloride (14.26 mmol, 1.040 mL, 1.696 g) added and the resultant solution stirred at room temperature for 45 min. The sample was concentrated and azeotroped with dichloromethane (×4). Potassium carbonate (21.39 mmol, 2.96 g) was added followed by DMF (20 mL) and (3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (7.13 mmol, 1.184 g) and the mixture heated to 60° C. for 1 h. The mixture was concentrated and partitioned between ethylacetate/water. The aqueous layer was twice extracted with ethylacetate and combined organics dried, filtered and concentrated to give a yellow oil which was purified on silica eluting with 0-1% MeOH/DCM to give (S)-benzyl-5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-ylcarbamate as a light coloured oil (2.67 g, 84%). 1H NMR (400 MHz, CDCl3) δ 1.83 (t, 1H) 2.79 (m, 2H) 3.27 (m, 2H) 4.51 (bs, 1H) 4.63 (d, 2H) 4.98 (bs, 1H) 5.08 (bs, 2H) 5.24 (s, 2H) 7.05-7.11 (m, 2H) 7.18 (m, 1H) 7.26-7.39 (m, 6H).

Workup

  1. concentrationThe sample was concentrated
  2. customazeotroped with dichloromethane (×4)
  3. concentrationThe mixture was concentrated
  4. custompartitioned between ethylacetate/water
  5. extractionThe aqueous layer was twice extracted with ethylacetate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. customwas purified on silica eluting with 0-1% MeOH/DCM

Sources & evidence

ORD record
ord-1e44daefd0074a3da9d471c2e5e783f7
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536214B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes