Boron Trichloride → HCID 57939302, compound

HRID 872239Notes

Reaction equation

HRID 872239 reaction equation
[Cl:1][C:2]1[C:11]([O:12]C(C)C)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:3]=1.B(Cl)(Cl)Cl>>[Cl:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 25135Boron TrichlorideHCID 579393587-Chloro-8-[(propan-2-yl)oxy]-5-(pyridin-3-yl)quinoline

Product 1

HCID 57939302HCID 57939302, compoundYield 94.6%

Procedure

Cleavage of the isopropyl ether 22 (20 mg, 0.07 mmol) with boron trichloride following the method outlined in Example 8, gave 7-chloro-5-(pyridin-3-yl)-quinolin-8-ol (PBT 1057) as a pale straw-coloured solid (17 mg, 94%). 1H NMR (CD3OD, 400 MHz): δ 9.16 (m, 2 H), 9.04 (d, J=5.8, 1 H), 8.93 (dd, J=1.2 and 8.6, 1 H), 8.84 (m, 1 H), 8.30 (dd, J=5.8 and 8.1, 1 H), 8.09 (s, 1 H), 8.08 (dd, J=5.1 and 8.6, 1 H).

Sources & evidence

ORD record
ord-3d9d3217ef2f4000ac09396326e50433
Source dataset
uspto-grants-2015_03
Patent number
US08975278B2

Reaction notes

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