HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

6-Bromo-4-fluoro-2,3-dihydro-1H-inden-1-one → (R)-3-[6-(2-Cyclopropyl-ethoxy)-pyridin-3-yloxv]-1-(7-fluoro-3-oxo-indan-5-yl)-pyrrolidin-2-one

HRID 533890
Notes
Print preview

Reaction equation

HRID 533890 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:12]=[CH:11][C:10]([O:13][C@@H:14]3[CH2:18][CH2:17][NH:16][C:15]3=[O:19])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Br[C:21]1[CH:29]=[C:28]2[C:24]([CH2:25][CH2:26][C:27]2=[O:30])=[C:23]([F:31])[CH:22]=1>O1CCOCC1>[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:12]=[CH:11][C:10]([O:13][C@@H:14]3[CH2:18][CH2:17][N:16]([C:21]4[CH:29]=[C:28]5[C:24](=[C:23]([F:31])[CH:22]=4)[CH2:25][CH2:26][C:27]5=[O:30])[C:15]3=[O:19])=[CH:9][CH:8]=2)[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 509894266-Bromo-4-fluoro-2,3-dihydro-1H-inden-1-oneHCID 86715085(R)-3-[6-(2-cyclopropyl-ethoxy)-pyridin-3-yloxy]-pyrrolidin-2-one

Product 1

HCID 86715084(R)-3-[6-(2-Cyclopropyl-ethoxy)-pyridin-3-yloxv]-1-(7-fluoro-3-oxo-indan-5-yl)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (R)-3-[6-(2-cyclopropyl-ethoxy)-pyridin-3-yloxy]-pyrrolidin-2-one (100 mg), 6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-one (87 mg) and 1,4-dioxane (2 mL) was purged with argon. N,N′-Dimethyl-ethylene-diamine (336 mg), cesium carbonate (248 mg) and copper(I) iodide (7 mg) were added. The mixture was heated to 85° C. for 3 hours. After cooling to r.t. the mixture was filtered and the filtrate purified by preparative HPLC to provide Example 1-08. 1H-NMR (400 MHz, DMSO) 67.99 (1H, dd, J=11.3, 1.8 Hz), 7.97 (1H, d, J=3.1 Hz), 7.77 (1H, d, J=1.8 Hz), 7.53 (1H, dd, J=9.0, 3.1 Hz), 6.77 (1H, d, J=9.0 Hz), 5.22 (1H, dd, J=8.3, 8.3 Hz), 4.24 (2H, t, J=6.8 Hz), 3.96 (1H, m), 3.86 (1H, m), 3.10 (2H, m), 2.72 (2H, m), 2.69 (1H, m), 2.14 (1H, m), 1.60 (2H, dt, J=6.8, 6.8 Hz), 0.80 (1H, m), 0.42 (2H, m), 0.10 (2H, m).

Workup

  1. customwas purged with argon
  2. additionN,N′-Dimethyl-ethylene-diamine (336 mg), cesium carbonate (248 mg) and copper(I) iodide (7 mg) were added
  3. temperatureAfter cooling to r.t. the mixture
  4. filtrationwas filtered
  5. customthe filtrate purified by preparative HPLC
  6. customto provide Example 1-08

Sources & evidence

ORD record
ord-de6cf50f497040b3a2c628c399cf3d4d
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853412B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes