Diiodoethane → HCID 53311312, compound

HRID 1854612Notes

Reaction equation

HRID 1854612 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.CC1C=CN=C(NC2C=CC=C(C3OC=NC=3)N=2)C=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[I:50]C(I)C>C1COCC1>[I:50][C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 68980DiiodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 53311228HCID 53311228, compoundHCID 53311311HCID 53311311, compound

Product 1

HCID 53311312HCID 53311312, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-iodooxazole derivative was prepared as for [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine above from (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine with LiHMDS (1M solution in THF) and diiodoethane in anhydrous THF to give the title compound as a yellow solid (41%) after purification by column chromatography on SiO2 eluting with 40% EtOAc in cyclohexane. 1H NMR (300 MHz, DMSO-d6) δ=9.81 (s, 1H), 8.10 (d, J=5.0 Hz, 1H), 7.84-7.51 (m, 4H), 7.23 (d, J=7.2 Hz, 1H), 6.77 (d, J=4.6 Hz, 1H), 2.33 (s, 3H).

Sources & evidence

ORD record
ord-55db21df8a534c34910011a2d7d6c548
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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