2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 4-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenol

HRID 908444Notes

Reaction equation

HRID 908444 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][C:2]=1[C:10]1[C:11]([NH2:27])=[N:12][CH:13]=[C:14]([C:16]2[CH:17]=NN(C3CCNCC3)[CH:20]=2)[CH:15]=1.[CH3:28][O:29][C:30]1C=C(B2OC(C)(C)C(C)(C)O2)C=[CH:32][C:31]=1[OH:45]>>[NH2:27][C:11]1[N:12]=[CH:13][C:14]([C:16]2[CH:20]=[CH:32][C:31]([OH:45])=[C:30]([O:29][CH3:28])[CH:17]=2)=[CH:15][C:10]=1[C:2]1[O:3][C:4]2[C:9]([N:1]=1)=[CH:8][CH:7]=[CH:6][N:5]=2

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 576871133-Oxazolo[5,4-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Product 1

HCID 673886644-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenolYield 101.6%

Procedure

Using the procedure described in the starting material portion of Example 41, 5-bromo-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (1 g, Example 9 starting material) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (902 mg) were reacted to afford 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenol (940 mg) as a solid. NMR Spectrum: (DMSOd6) 3.89 (s, 3H), 6.87 (d, 1H), 7.11 (dd, 1H), 7.25 (d, 1H), 7.53 (dd, 1H), 7.74 (bs, 2H), 8.29 (dd, 1H), 8.39 (dd, 1H), 8.44 (d, 1H), 8.57 (d, 1H), 9.11 (bs, 1H); Mass spectrum: M+H+ 335.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6b64f2279ff5457fa1997d4876fe7404
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

Loading…