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

Sodium Carbonate → HCID 72549195, compound

HRID 1022440
Notes
Print preview

Reaction equation

HRID 1022440 reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][N:11]([CH2:12]C)[C:4]=2[CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][N:11]1[C:4]2[CH:3]=[C:2]([C:19]3[CH:20]=[CH:21][C:16]([C:15]([F:26])([F:25])[F:14])=[CH:17][CH:18]=3)[NH:7][C:6](=[O:8])[C:5]=2[CH:9]=[CH:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86704560HCID 86704560, compound2×

Product 1

HCID 72549195HCID 72549195, compoundYield 109.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A microwave reaction vial was charged with 6-chloro-1-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (Intermediate G) (16 mg, 0.08 mmol), 4-(trifluoromethyl)phenylboronic acid (20 mg, 0.10 mmol), tetrakis(triphenylphosphine)palladium(0) (5.06 mg, 0.004 mmol), and 2M aqueous sodium carbonate solution (0.13 mL) in ethanol (2 mL). The vial was sealed and then heated in a microwave at 140° C. for 10 min. At this time, the resulting mixture was filtered through a pad of Celite® and concentrated in vacuo. Flash chromatography (20/1 methylene chloride/methanol) afforded 1-methyl-6-(4-trifluoromethyl-phenyl)-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (25.6 mg, 39.1%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.8 (s, 3H) 6.5 (d, J=3.01 Hz, 1H) 7.0 (s, 1H) 7.1 (d, J=3.01 Hz, 1H) 7.8 (d, J=8.28 Hz, 2H) 8.0 (d, J=8.28 Hz, 2H) 11.1 (br. s., 1H). LC-MS calcd. for C15H12F3N2O [(M+H)+] 293, obsd. 293.0.

Workup

  1. customA microwave reaction
  2. customThe vial was sealed
  3. filtrationAt this time, the resulting mixture was filtered through a pad of Celite®
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b6846b2c7fa4361b35a72a4634471a3
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722661B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes