Pyridine → 1-(3-Fluoro-5-iodopyridin-2-ylamino)-2-methylpropan-2-ol

HRID 629204Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([I:9])=[CH:4][N:3]=1.N1C=CC=CC=1.[NH2:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19]>CN1C(=O)CCC1>[F:8][C:7]1[C:2]([NH:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])=[N:3][CH:4]=[C:5]([I:9])[CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2,3-Difluoro-5-iodopyridine (500 mg, 2.07 mmol) was dissolved in NMP (500 μL) and pyridine (201 μl, 2.49 mmol, 1.2 equiv.) and 1-amino-2-methylpropan-2-ol (555 mg, 6.22 mmol, 3 equiv.) were added at room temperature. The mixture was stirred for 16 hours at 100° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired 1-(3-fluoro-5-iodopyridin-2-ylamino)-2-methylpropan-2-ol (590 mg, 1.9 mmol, 91.7% yield) was obtained as a colorless oil, MS: m/e=311.0 (M+H+).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane
customThe crude product was purified by flash chromatography
washeluting with an ethyl acetate

Sources & evidence

ORD record: ord-3b97cf8d77f14e17903e620e5e3ceca5
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315498B2

Reaction notes

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