Dichloromethane → HCID 117601990, compound

HRID 1773720Notes

Reaction equation

HRID 1773720 reaction equation
[CH:1]1([N:4]2[C:8]3[C:9](I)=[CH:10][C:11]([C:13]4[C:14]([CH3:19])=[N:15][O:16][C:17]=4[CH3:18])=[CH:12][C:7]=3[NH:6][C:5]2=[O:21])[CH2:3][CH2:2]1.[CH2:22](Cl)Cl.[CH2:25]1[CH2:35][CH2:34][N:33]2[C:28](=N[CH2:30][CH2:31][CH2:32]2)[CH2:27][CH2:26]1>CS(C)=O.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]>[CH:1]1([N:4]2[C:8]3[C:9]([C:26]4[C:25]([CH3:22])=[CH:35][CH:34]=[C:28]5[C:27]=4[CH:30]=[CH:31][CH:32]=[N:33]5)=[CH:10][C:11]([C:13]4[C:14]([CH3:19])=[N:15][O:16][C:17]=4[CH3:18])=[CH:12][C:7]=3[NH:6][C:5]2=[O:21])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 117600984HCID 117600984, compound

Product 1

HCID 117601990HCID 117601990, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
140 °C

Procedure

To a microwave vial containing 1-cyclopropyl-5-(3,5-dimethylisoxazol-4-yl)-7-iodo-1H-benzo[d]imidazol-2(3H)-one (25 mg, 0.063 mmol, 1 equiv.) was added 3,5-6-methylquinolin-5-ylboronic acid (71 mg, 0.38 mmol, 6 equiv.), Pd(dppf)Cl2.CH2Cl2 (11 mg, 0.013 mmol, 0.1 equiv.) and DBU (76 mL, 0.51 mmol, 8 equiv.) and dissolved in DMSO-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 140° C. for 30 minutes in the microwave reactor. Purification was carried out by reverse phase HPLC.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-badaf30d7a1c4e93912e8bb450fa3461
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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