Sodium Carbonate → HCID 89561194, compound

HRID 1477364Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5](I)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:17]1(B2OC(C)(C)C(C)(C)O2)[CH2:19][CH2:18]1>CC#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:17]2[CH2:19][CH2:18]2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Chloro-5-iodo-N-methylpyridin-4-amine (Intermediate I-8) (30 mg, 0.112 mmol), tetrakis(triphenylphosphine) palladium (0) (6.5 mg, 5.59 μmol) and 0.5 M aqueous sodium carbonate solution (290 μL, 0.145 mmol) were added to 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61 μL, 0.335 mmol) in MeCN. The mixture was heated at 130° C. in a microwave reactor for 1 hour. The mixture was concentrated in vacuo. Preparative thin layer chromatography, eluting with 1% NH3, 6% MeOH in CH2O12, gave 2-chloro-5-cyclopropyl-N-methylpyridin-4-amine (10 mg, 0.055 mmol, 49% yield) as a white powder.

Workup

concentrationThe mixture was concentrated in vacuo
washPreparative thin layer chromatography, eluting with 1% NH3, 6% MeOH in CH2O12

Sources & evidence

ORD record: ord-167ed020ba324db38c799eda6cbc31ab
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403797B2

Reaction notes

Loading…