N-methyl-2-pyrrolidone → HCID 90015001, compound

HRID 1057063Notes

Reaction equation

HRID 1057063 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([Cl:14])[N:3]=1.Cl.[F:16][C:17]1([F:22])[CH2:21][CH2:20][NH:19][CH2:18]1.CN1C(=O)CCC1.CCN(C(C)C)C(C)C>>[Cl:14][C:4]1[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[C:2]([N:19]2[CH2:20][CH2:21][C:17]([F:22])([F:16])[CH2:18]2)[N:3]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 57643150HCID 57643150, compound

Product 1

HCID 90015001HCID 90015001, compound

Conditions

Temperature
140 °C

Procedure

To a solution of 2,6-dichloro-4-(3-pyridyl)pyridine (48 mg, 0.21327 mmol) and 3,3-difluoropyrrolidine hydrochloride (153 mg, 5.0 equiv., 1.0663 mmol) in NMP (1.0 mL, 10 mmol) in a microwave vial was added DIPEA (0.26 mL, 7.0 equiv., 1.4929 mmol), and the reaction was maintained at 140° C. for 60 min then at 150° C. for 20 min in the microwave machine, while LCMS indicated the conversion was more than 95%. The crude was used without further treatment. LCMS: m/z 296 (M+H).

Sources & evidence

ORD record
ord-520a16c7036b46ffaa306bdcda27d566
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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