Imidazole → HCID 87214270, compound

HRID 2066679Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11]O)=[CH:4][CH:3]=1.[I:22]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH:10]([CH2:11][I:22])[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:6][N:7]=1

Participants

Reactant 4

HCID 795Imidazole

HCID 807Iodine

HCID 11776Triphenylphosphine

HCID 87214437HCID 87214437, compound

Product 1

HCID 87214270HCID 87214270, compoundYield 97%

Procedure

Iodination of alcohol 187 with I2, PPh3 and imidazole as in Example 2GGG above for 18 h, followed by chromatography of the product on silica gel, eluting with petroleum ether and pentane (foreruns) and then with 5-25% Et2O/pentane, gave 2-bromo-5-[3-{[tert-butyl(dimethyl)silyl]oxy}-2-(iodomethyl)propoxy]pyridine (188) (97%) as a colourless oil; 1H NMR (CDCl3) δ 8.07 (d, J=3.0 Hz, 1H), 7.37 (dd, J=8.7, 0.3 Hz, 1H), 7.11 (dd, J=8.7, 3.2 Hz, 1H), 4.06 (dd, J=9.2, 5.7 Hz, 1H), 3.99 (dd, J=9.2, 6.1 Hz, 1H), 3.74 (dd, J=10.1, 5.6 Hz, 1H), 3.70 (dd, J=10.1, 5.5 Hz, 1H), 3.36 (d, J=6.0 Hz, 2H), 2.12 (sept, J=5.8 Hz, 1H), 0.89 (s, 9H), 0.06 (2 s, 6H); HRESIMS calcd for C15H26BrINO2Si m/z [M+H]+ 487.9935, 485.9955. found 487.9931, 485.9952.

Workup

customabove for 18 h
washeluting with petroleum ether and pentane (foreruns)

Sources & evidence

ORD record: ord-eb503b886633492789ded9f1c8a63cdc
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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