Dichloromethane → HCID 71283092, compound

HRID 335290

Reaction equation

HRID 335290 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=3[F:24])[C:17]([O:19]C)=[O:18])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:25][N:26]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27]1.C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:24][C:23]1[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[NH:13][C:11]([C:8]1[N:5]2[CH:6]=[CH:7][C:2]([C:29]3[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=3)=[CH:3][C:4]2=[N:10][CH:9]=1)=[O:12]

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 10340Sodium Carbonate2×HCID 10796Cesium carbonateHCID 112635011-Methyl-1H-pyrazole-4-boronic acidHCID 712828883-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester2×

Product 1

HCID 71283092HCID 71283092, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture comprising methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluorobenzoate (Intermediate 1A) (5.41 g, 13.79 mmol), 1-methyl-1H-pyrazol-4-ylboronic acid (1.911 g, 15.17 mmol), Pd(dppf)Cl2.DCM (1.127 g, 1.379 mmol) and cesium carbonate (13.48 g, 41.4 mmol) in DME (100 ml) and water (10 ml) was heated at 100° C. for 4 hrs. 3 equivalents of sodium carbonate were added and the mixture was heated to 100° C. for 6 hrs. A further 3 equivalents of sodium carbonate were added and the reaction was heated at 100° C. overnight.

Workup

  1. temperaturethe reaction was heated at 100° C. overnight

Sources & evidence

ORD record
ord-ef6c0f870f63447f98a9040e80ba6368
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Linked notes

Loading…